Exploits – Life with Barbara Part One
Barbara was a phase of my life like no other and will be far the larger amount of stories. A lot of these, if you’ve read my previous work, might sound familiar since I’ve used them or parts of them for some of my fictional work. Of course the names have been changed to protect the guilty.
Barbara came into my life entirely by accident. I’d moved into a small apartment not far from the school where I worked and had fully accepted my bisexuality and desire to wear lingerie. Amber had enjoyed a six month relationship with a married lover (a ‘sugar daddy’ as Barbara called him after I’d told her about him) that had moved and I had pretty much decided to go steady with Rosy Palm for a bit and save up some money. I’d spent most of Friday and Friday night doing the same thing and all I had to show for it was a clean kitchen and most of my clean clothes put away. I had cum once on Friday but hadn’t rushed that one either.
There was a bar I frequented with a totally straight crowd that I’ll call “Frank’s Place” in these stories. Frank was an older man and had decided to shut the bar for a week to take his wife someplace special for their 50th anniversary. He promised to be back to open on Labor Day weekend. The gang, male and female, that gathered to watch Cowboys football decided that another bar down the street called “The Corner” would be our meeting place to watch the Cowboys game on Sunday.
So once again I had nothing planned until Sunday and Saturday I’d spent a leasurely morning sipping wine, smoking dope, running around in my favorite nightgown, or cock in hand, reading erotic stories, and edging. I was keeping myself aroused but holding off, enjoying the super sensual feeling of being stoned, in sexy lingerie, and highly sexually stimulated at the same time. Unfortunately, or fortunately as it turned out, I closed my eyes to picture myself as the person in a story I’d just read, as I’d been doing all morning, and nodded off. When I woke up, it was late afternoon, I was out of wine, and almost anything edible.
I jumped in the shower and then dressed in clean panties and male outer attire, did my grocery, beer, and wine shopping and on a lark, decided to stop at the bar where we’d agreed to meet the next day.
In the crowd that had gathered were two women, mid-30’s, equally attractive, and I really didn’t know either of them. One was a short brunette with a smoldering look that promised great things but was pretty much an unknown. She was recently divorced and spent most of her socializing time at the Corner. The other was a cowgirl I’d fantasized about a few times since I’d been told she could suck a golf ball through a garden hose. The brunette was quiet and watchful and several times I caught her watching me. The cowgirl was her usual loud and brassy self so I decided I’d see how far I could get with the brunette.
We quickly became equally infatuated with each other and by the time the sun set we both knew we’d be spending the night together. Using the excuse that we were going to go get something to eat, we took off in my car.
The meal part was real. Neither of us had eaten lunch and we were both starved, but I knew as soon as the meal was done, we’d be coming back to my apartment and I’d left things laying around that I didn’t want her to see. Aside from the books and magazines, I’d left my nightie thrown on the bed and a dildo on the nightstand and couldn’t remember what else might be left where she might notice.
She was curious when I pulled up in front of my apartment building but told her I’d be right back that I wanted to get a pack of cigarettes and then left her sitting with the motor running. I was on the second floor and had just reached the stairs, when I heard her shut off the motor and tell me she needed to use the bathroom.
Crap! I flew up the stairs, grabbed everything incriminating that I could find and tossed it under the bed and barely made it before she’d followed me into the bedroom and then popped into bathroom. I’d made a quick glance in there and hadn’t seen anything and when she came out, she seemed like nothing had changed. She asked where and what was I planning to eat and I told her what I really wanted was to eat her right here on that bed. She said that’s what she wanted too but . . . she really was hungry and she needed to be home to get a call from her sister, so we headed out to eat.
Instead of going to my place for dessert, which by then we’d agreed would be each other, she insisted I spend the night at her place and at that point I wasn’t about to argue; especially since she’d added, “and next time we can go to your apartment.”
Let me pause the story to point out something my experience with women had taught me. Most, including my ex-wife the whole time we were married, will turn their back to you when they undress. For me, that was always a blessing since I was often wearing panties. I’d dawdle taking off my boots, and then as soon as they’d turn their back, I’d pull down my panties and jeans together. I’d done that successfully several times and it worked that night with Barb too.
If ever I was going to have sexual stage fright it would have been that night. I’d been promised an encore performance before she’d ever seen my act. I was fully prepared to do whatever it took for however long it took to rock her world. My plan was to make her orgasm at least once with my tongue before we got to the ol’ in and out part. So I licked and I nibbled and I sucked and caressed and nibbled and licked some more and would have been at it at sunrise had she not stopped me and told me that if I was trying to make her cum it wouldn’t work – she couldn’t cum that way.
Fine. Not a problem - I hoped. I knew some women require penetration and I just hoped she wasn’t used to a much bigger penetrator than mine. We commenced to fucking and fucking and fucking. I tried different positions and techniques and wasn’t getting anywhere. I’m doing quadratic equations in my head trying to get her to cum before I do. Finally I gave up and gave her the big load of cum I’d been holding back since that morning.
I was spent in more ways than one. I couldn’t remember ever having cum that hard and there wasn’t an ounce of energy anywhere in my body. I was too wasted to even roll off of her. Then I heard her tell me, as I felt her hand squeeze in between us, to get off, that she needed to cum.
As I rolled to one side she began to finger herself. She wanted to masturbate to orgasm because I had failed to perform for her. Bullshit, I thought. I’m not giving up yet.
Quickly I got between her legs and moved her hand out of the way and went after my favorite post coital meal – a cream pie! I love cum and mixed with the juices of a freshly fucked female it’s even better. Within seconds I had her flopping around on the bed like a fish out of water and making noises that should have had someone calling the law. Then she had an orgasm and fainted.
For a moment I really thought she’d died. I’d heard about old men having heart attacks and dying in bed but never 37 year-old women. I was speaking to her, squeezing her hand, looking for some sign of life and wondering what I’d tell the 911 dispatcher to explain the situation when she took a big breathe, opened her eyes slightly, mumbled ‘goodnight’ and went out. I wasn’t far behind her.
The next morning was almost a repeat. I’d gotten up to drink about a gallon of water and was headed to the bathroom when she called me back to bed. I remembered what she’d said about not being able to cum from me eating her pussy, but that didn’t make sense because that was what finally got her off. However I knew what had worked the night before, and repeated it all but in a much shorter time and again got the same result. While licking my cum out of her she exploded.
By then I desperately needed to pee. However she recovered first and headed to the bathroom. When I heard the toilet flush I headed that way and as I entered, she turned on the hot water, told me it took a few minutes to get warm, that I was welcome to shower with her, and then told me she’d be right back. I gave her a quick kiss, turned to the toilet, and found the seat down and piled with towels and hair stuff. I thought about moving it, then decided I’d just get in the tub and pee in the tub drain. Good plan but… t just about the time I was ready to pee, she stepped into the tub in front of me and bent over to adjust the water temperature.
Feeling frisky, and maybe just a little drunk from the night before, I began to pee between her legs and then raised my aim until I was pissing on her slit. I thought she’d jump but instead she leaned over further and rotated her hips so I could pee on her clit.
When I’d finished, she turned around and asked why I’d done it and since it had been totally unplanned with no conscious intention other than playing around I told her that I was hoping she’d return the favor.
If you haven’t read about my life prior to this, then let me tell you that pee play or ‘water-sports’ has been one of my favorite kinks since the start of puberty. It probably began a long time before that but it was in puberty that it took on sexual aspects.
I could have shrugged off her question and told her I was just fooling around, needed to pee and she’d stepped in the way. Telling her that I hope she’d return the favor was just to see how she’d react to trying something kinky. I was super happy when she told me to lie down on the floor of the tub and she’d try, that she’d never peed standing up but if I was serious, she’d be happy to try.
Unfortunately, she’d used the toilet minutes earlier so I was too late and we laughed it off. She told me to shower first, that she needed to wash her hair and if I wanted a beer, there was some in the fridge. I did, got out, dried off, and went for a beer and congratulated myself on finding what appeared to be the perfect woman. When I heard the water cut off, I went to ask her if she wanted a beer and she turned it down and began to tell me her plans for the day as she dried her hair.
The reason we had to go to her place the night before was a family meeting that afternoon. Her mom was going to be at her sister’s house and they were all having a family meeting to discuss what to do with her mom, that she needed to be put in a home. Then we talked about after and came up with a plan to meet back there, that I’d bring everything to fix a couple of steaks, bake some potatoes, and make a salad. That decided, she plugged in her hair bonnet and I went to get dressed.
Since she was in the bathroom with her hair dryer going, I felt it was safe to pull my panties out of my jeans and put them on first. So I was standing in her bedroom, wearing nothing but a pair of panties, when she walked in. She’d decided to do her makeup while her hair was drying, needed something off the dresser, and had unplugged the air hose but left the dryer motor going. She looked at my panties, said, “That’s cute,” and went back to the bathroom.
That gave me a lot to think about and the whole afternoon that’s all I thought about. We were obviously attracted to each other. I’d revealed part of my kinky side and she hadn’t given any negative responses. Her only comment on my eating her cream pie and giving her an incredible orgasm again that morning had been, “I can’t believe you did that.” I wasn’t sure how she meant it, but it wasn’t negative. She’d kissed me and sucked my tongue half-way down her throat. Then she’d told me my panties were ‘cute’ and in my experiences, when a woman told me that or something similar, they were okay with it.
By the time I was ready to change and head back to start on our cookout, I’d decided to push the feminine side of me a bit. I wore a similar pair of panties, ladies shorts, a t-shirt and ladies sandles. I almost wore a bra, but decided that would be pushing it and I’d see how it went. I was sure we’d be having sex again that evening and I’d take my time undressing to see how she reacted to the panties. The shorts were cutoff, sequined and embroidered, ladies jeans. I’d built up a collection of women’s casual wear that resembled men’s clothes from a distance but up close if you paid attention, they were definitely feminine.
She’d given me a key, so I had the fire started, the potatoes baking, and was making the salad when she got home. She came in with a big suitcase, set it down, gave me a great kiss, and at the same time opened the shorts and let them drop to my ankles. She followed them down and pulled my swelling cock out over the top of my panties and began to give me a world class blow job, not stopping until my knees buckled and she had a mouth full of my baby batter. I pulled her up off her knees when I’d regained the strength in mine and kissed her and when we broke the kiss, she gave me a funny look and asked, “Doesn’t it bother you that I just sucked your cock?”
“Of course not,” I told her. “Why should it?”
“You’re different,” she commented, more like she was thinking that to herself and then walked off.
I considered wearing just the t-shirt and panties like women do all the time, but there were neighbors to consider if I was going to put the steaks on the grill on the back porch. However she had several opportunities to see me dressed in those panties and never made a comment.
I should explain that those panties were a gift from John, the man I referred to earlier that had been my lover and had recently moved. He was the manager of a large discount chain store in a nearby shopping center and often gifted me with lingerie. These panties – there were five in the set – were novelty panties. They were all white with a different street sign in front and matching lacy colored edge. The pair I’d been wearing the night before and earlier that morning had a triangular yellow “Yield” sign on the front with the words “TO ME” just below and yellow trim at the waist and legs. The ones I’d had on that afternoon had a red octagon “STOP” sign and just above it the word “DON’T” and were trimmed in red. Another, trimmed in black had a one way sign with the arrow pointing down, another had a “Proceed with Caution” sign – you get the idea.
The bottom line here is that she never said a word about the way I was dressed and we made a date for the following weekend, with her agreeing to stay at my place on Saturday night and we’d play it by ear from there. It was Labor Day weekend and the only thing we both wanted was to spend all three days and nights together. I promised to call mid-week and that was where we left it when I left for work Monday morning.
I’m sure I told her that I was taking night courses at our community college. The school where I worked was super busy with new students coming in and classes beginning the next week. I had finals all week at the school where I was going and it was almost accidental when I reached her from work on Friday morning. She was pissed but when she’d calmed down and listened to my story it made sense. I had a window of opportunity to call her at noon and between work and night school and when I got home it was after ten and I didn’t want to call that late. I wasn’t supposed to make personal calls at work but had in this case since to me it was nearly an emergency. She’d never told me she did volunteer work during the day, stopped at the Corner on the way home, and by the time she got home I was in school. She’d been thinking about getting an answering machine but hadn’t as yet. I’d written down my number for her but she’d lost it.
However we got it straightened out and confirmed our plans for her to come over Saturday and spend the weekend with me. By the time we finished that call we were both damn near having phone sex.
I would have preferred to start our weekend on Friday night but my apartment needed to be put in order for my full revelation. I had a huge stack of the letter magazines popular in the 70’s and 80’s like Variations, Penthouse Letters, and similar publications. They were full of letters from people concerning a variety of sexual practices. All of the ones that had stories about bisexual men, cross dressing, pee play, and wearing and wetting diapers had the stories ear marked and a color code of stripes on the bottom of the magazine. I had begun to sift through them looking for stories about bisexual cross-dressing men in successful relationships with a woman and setting them in a separate pile. My plan was to tell her about myself, and then let her read a few of the magazine stories in hopes that it would encourage her to try a relationship with me.
I began cleaning Friday as soon as I got off work, finished sorting the magazines, and then Saturday morning hand washed my lingerie and put it out on a clothes line I’d installed on the long back porch behind my apartment and the one next to it. The lady that lived next door to me was aware of my sexual perversions and thought it was harmless.
Friday night had been date night with John, something we’d added the last few months before he moved. The store was open until 10 so I’d be dressed to go out at 6 and he’d take me to diner fully dressed as a woman. Maybe in memory of him I’d started dressing as if I was going out but had stopped with after putting on my lingerie. I’d picked out a matching bra and panty set, stockings and garter belt, and stuffed the bra with the breast forms John had gotten for me. Then instead of putting on a wig, makeup and dress, I’d put on a nightie and gone to work sorting the magazines, resisting the urge to pump one out. When I’d gotten up Saturday morning, with all the housework ahead of me, I’d changed out of the nightie into a house dress and when I had everything as neat and clean as it was ever going to get, I decided it was time to stock the refrigerator and pantry for the weekend. It was just after lunch, too early to change to get ready for Barbara, so I took off the housedress and slipped on some jeans, loafers, and a shirt and went to the store.
On the way back, I saw that “Frank’s” was open and must not have been for long because there was only one car and it was Frank’s. So I pulled in to have one beer and say hello. Barbara was sitting at the bar.
Since I was still wearing stockings and no socks, I couldn’t sit down or the taupe seamed hose would have been noticeable at my ankles. I was afraid if I hugged her she’d feel the padded bra under my shirt and light windbreaker that I’d added to hide the bumps the pads made. So I gave her a peck on the cheek, stood beside her and ordered us both a beer. She told me she’d just walked in, that her car was in the shop around down the street a block, and that she needed a ride home. Of course I offered, told her I’d drop her off on the way home and come back for her later. Everything looked like it was going to work out great until we got to her apartment and when she got out, she told me to wait a minute.
It was much more like five or ten, but she came out with an overnight case and a big smile. She was ready for our weekend to begin and I wasn’t.
I tried to make excuses about why she should wait, that I didn’t have the place ready and every other reason I could think of. Suddenly she blew up. She accused me of being married or having a girlfriend. She told me she’d seen a pink nightgown hanging on the back of the door when she’d used bathroom the previous week. She said I’d lied and that the reason I hadn’t called her was that my girlfriend was listening. She told me that there’d been a tray of makeup under the bathroom sink and she’d seen a makeup mirror on my dresser. When she’d finally worn down after calling me six kinds of a no good lying bastard, I started the car and never said a word. She kept asking questions about where we were going but stopped when she realized it was toward my apartment. She got concerned when I pulled into a driveway behind my apartment but stopped when I did. She was confused.
My apartment building was on the side of a hill and behind my apartment was a long concrete retaining wall. Above that was the driveway for the building behind me and parked where we were, we were almost level with my second floor apartment.
I’d turned off the motor and told her she was right, that there was another woman in my life. Then I pointed out her window and said, “See anything on that clothes line you might recognize?”
She looked for a minute and said she didn’t think so.
“How about that pink nightgown you said was in the bathroom? Or those white panties with the street signs on them?’
She looked again, then turned back to me kind of wide eyed.
“I’m the other woman,” I told her. “All those things are mine. If you want to come inside I’ll explain it. I’d planned to do that this weekend but you’ve made me do it early and in an uncomfortable way for both of us. I told you I had a surprise for you and this is it. If you want me to take you home I will but I ask you to please not say anything. This part of my life is my secret and I’d hate to have to find a new place to watch the Cowboys games.”
It took a moment or two longer than I’d hoped, making me very nervous, but finally she smiled slightly and said she wanted to stay at least to hear what I had to tell her.

Not only did she hear my story, she read all the magazines I’d earmarked for her, and then read all the other earmarked stories that I hadn’t intended for her to read. Each time she read a story that she didn’t understand, or didn’t understand why I liked it, I’d take time to explain it to her. I changed back into the housedress and left her at the table reading. As she read and sipped the glasses of wine I was giving her, I began making our supper, took the lingerie off the line and folded it and put it away. Every so often she’d make a comment about one of the stories but the only comment she made about me was when she read a story about a guy confessing to his wife that he loved her but he also loved to suck cock and loved the taste of cum and that was why he always ate her pussy after they fucked. She told me about the story then said, “You must be like this guy,” smiled at me and when I nodded, she went back to reading some more.
I smiled too. So much for having to tell her I was bisexual.
It wasn’t until after we’d eaten and were cuddled together on the recliner that she opened up about how she felt. She told me briefly that she’d had sex with one guy before she met the boy that she married while still in high school, that he got her pregnant and that they’d gone to Mexico to get married. No stranger to the problem, the Mexican officials had asked what date they wanted on the marriage certificate so they’d back dated it three months. Then her husband, David, had joined the Army and a few months later told them he’d met a woman with a new baby and the dad had died and he was going to adopt the baby and somehow he pulled it off. She’d had two more kids, one which had died as a baby, and that her two kids were now teens and living with her sister. She gave me a few more details and then asked if I still intended to take a shower and when I said I did, she grinned.
When I’d talked to her Friday and told her I had a surprise for her, she’d told me she had a surprise for me too. She followed me into the shower and told me not to turn the water on, that all week she’d been practicing peeing standing up and that if I really wanted her to pee on me like I’d said, and like she was sure I did since she’d found a couple of stories about that in the stack of magazines I hadn’t intended for her to read.
When I looked back on it, I think her peeing on me in the shower was her way of telling me that my fetishes were okay with her. We talked well into the night about what kind of relationship we could have. She’d been single again for only two months, after sixteen years of marriage, had been to bed with four men besides me in the last month and didn’t want to hop into another committed relationship until she’d enjoyed a variety of men.
Sunday we talked more, before, during and after our fucking and sucking each other senseless, and then on Monday, since neither of us had paid the Sept. rent, we decided to move in together at her apartment and my name was added to the lease. Under Texas laws we had a common law marriage and under the mores of the 70’s we had an open marriage. One thing for sure, it was one helluva crazy ride!

Part Four
At thirty years of age, I was divorced and set free on the world. I had behaved myself long enough and ready to partake of all the ‘free love’ and other sexual freedoms that had swept the country. In the last ten years I’d been in the Army, in college and married for five years and each had restricted me from some of the fetishes of my earlier years. Through it all I’d managed to keep a small stash of lingerie that I could wear when the opportunity arose. My ex had allowed it at times, but not near as often as I would have liked. And in the back of my mind at all times was how shamelessly I’d wanted that soldier’s cock after he’d offered it to me.
One of my top priorities was doubling or trebling my feminine wardrobe and I began to wear panties as my normal underwear and slept in a nightgown at night and that led to my first adulterous affair and having a woman that fully understood me.
Suzie was the young wife of a guy that had been one of my neighbors growing up. We’d crossed paths a few times over the intervening years and one day he showed at the bar I frequented and I learned we were neighbors again and didn’t know it. He invited me over for a weekend bar-b-q and there was a lot of drinking and Suzie came on to me. She knew I was now single, living alone and working from home and flat out told me she wanted to visit me some morning. I didn’t tell her yes, but I didn’t tell her no either.
I’ve always been an early riser so in spite of a hangover, I’d gotten up one morning, slipped out front to get the paper, started the coffee, and went back to bed. A couple hours later, I come out of a beautiful dream to see a naked woman sitting on the edge of my bed, running a finger up and down the bottom of my erection through the material of my nightgown and panties.
It was Suzie. I’d forgotten to lock the front door. As further testimony to how my lifestyle had changed after my divorce, my bedroom windows were covered with aluminum foil and I’d disconnected my doorbell, and habitually unplugged my phone until I was up and felt like dealing with the world. She’d tried to call, had come by and saw my car in the driveway, found the front door open and the screen door unlocked and let herself in. When she found me asleep in a baby-doll nightie, she undressed and woke me by playing with my dick.
For the next year or so, not only did we have great sex, but we also had great talks about sex and all the things two people could do, including the things we could do with our own gender. She admitted to having had sex with Don’s brother, and two women, one of which she was still seeing, and I told her every detail about my sex experiences and dressing as a girl in my youth and she was most fascinated hearing me describe sucking cock. Then we moved on to fantasies and things we’d like to try and if it was something a man and woman could do, we did it. I readily admitted that I was eager to suck cock again but not so eager that I was going to a gay bar to find some stranger. I’d heard that STDs were rampant in the gay community.
She bought me a dildo and had me suck it while she sucked mine and I’d told her how I’d enjoyed cream pies, how the first had led to my first fuck and that’s why I always licked her pussy after we fucked, that it was a win-win sexually. She got extra orgasms and I got to taste cum. That confession had led to her insisting Don fuck her before he left for work and as soon as he was gone, she was at my house feeding me his cum. You gotta love a woman that takes care of the basic needs of two men at the same time.
Another of the fun things we did was shop together. When she decided that we should have matching nightgowns I told her we should pick them out together and I’d pay for them and off we went. We had so much fun we added that to the sexual side of things. One thing that made it fun was her constantly reminding me I was a sissy cocksucker. It didn’t matter if we were walking down a mall concourse, eating in a restaurant, or browsing a department store, she’d point to a mannequin or woman and tell me I’d look good in the clothing. She’d point out a guy’s package and comment we should ask him if he wants a blowjob. One time in a JC Penny store she held some bikini panties in front of me with the sales lady watching and said, “You’d like nice in these, but it would make you hard and they’re not big enough.” I thought that salesclerk was going to choke. Needless to say, when we went in there again a couple of weeks later, she remembered us.
So I was constantly being reminded of my sissy side, even if I had Suzie and a few other women in my life at the time. Then a guy I’d worked for part-time asked if I’d go to Midland to finish a project for him, that the man that had started it had quit and he was in a bind. I agreed, packed a couple of suitcases, and jumped on a plane to Midland.
For about a month I was living and working out of a motel room. The second week I was there the manager came to me on a Saturday morning asking a favor. Another of the long-term tenants had gotten thrown in jail for public intoxication and needed him to bail him out and he was by himself and asked if I’d go do it. I agreed and after I’d sprung the guy, he offered to buy my lunch and I agreed to that too.
I think his name was Tom. He was a graduate student writing his thesis about something to do with the societal aspects of the Permian Basin oilfields. Occasionally he had to go do some research or interview someone but other than that, he was around the motel most of the time. The next morning when I went out to the pool he was there, and we talked.
We both planned to kick back and watch the Cowboys’ game later in the day. A bit later he knocked on the door and asked if I’d run him to the store. I had a rent car, and he didn’t and during the trip he suggested we watch the game together, that the TV in his room was screwy and that he’d buy the beer and snacks. I thought that was a good idea but what I hadn’t counted on was him following me into my room when we got back, saying he had to pee, and going straight into the bathroom.
I’d been wearing my bathing suit that morning because I was out of clean underwear and after handwashing all my lingerie, I’d hung it to dry on the bathroom towel bars, curtain rod, and an improvised clothesline. The clothesline went from the showerhead to a coat hook, and unless he sat to pee, he must have had a pair of panties in his face the whole time he was pissing. When it came time to watch the game, he laid back on the bed and after a few minutes he said he really should take his shoes off. I made some comment like, “Sure, get comfortable” and next thing he’s down to his underwear.
That’s when I knew something was going to happen and it became definite when he said I’d probably be more comfortable in a nightgown, and he wouldn’t mind if I wanted to wear one. I did. Knowing where this had to be leading, I wanted to be dressed in lingerie. By the time I had the nightgown on, he was stroking a nice-looking erection, and I couldn’t get it in my hands and mouth quick enough!
My ten-year dry spell, or in my case, ten years of not having a cock to suck, wasas over. I was savoring the flavor of a sweet load of cum before the opening kickoff and I doubt I saw any of the game. We took turns sucking each other and we did it slowly.
It was beautiful, sensuous, and so satisfying to have my mouth on a cock again after the ten years since I’d sucked off that soldier and Tom understood my need. The third time I began sucking him he asked how long it had been and when I told him ten years, he’d nodded and told me “I understand,” then laid back to let me enjoy myself. He realized I was trying to make up for lost time.

That began five years of confusion. I don’t know how to put it any other way. The biggest part of the problem was a story I’d read in Playboy or Penthouse by a supposed expert on such things that said that people that claimed to be bisexual were just gays in denial. Susie and I had discussed that at length and were sure we were both bisexual and yet, not long after I got back from Midland, she told me she was leaving Don and planned to live with one of the women she’d been having sex with and not long after that the two moved to California to live as husband and wife. I wasn’t surprised really – she’d told me she didn’t enjoy sex with Don, and that the reason she loved sex with me was because I had such a strong feminine side. She saw me more as a masculine woman than as a feminine man.
That meant that in my mind, I had to scratch the whole ‘bisexual’ thing as gay in denial. The expert had to be right. Suzie had only been fooling herself thinking she was bi and I must be doing the same thing. I was really gay and just didn’t want to admit it, even to myself.
With that decided, for a few months I was an avid sissy cocksucker, wearing lingerie, hanging out in gay bars, craving cock and cum. But there was a problem. I didn’t really like men that much. Even the few that I met that I had something in common with weren’t of interest to me except in feeding me their cocks. I missed the intimacy of having sex with a woman and while I wasn’t really looking for one, I’d eventually come across one that showed interest in me, and my normal male side would have me in a relationship before I knew it.
And it would be great! I love women. I loved sex with women. I’d introduce them to my feminine side and usually they accepted and sometimes wanted to expand it. I’d conclude that my cock sucking binge had gotten it out of my system and having a woman in my life that was okay with the woman in me was all I’d needed. And eventually that feminine side would do me in. I really missed sucking cock and I’d dump the woman and begin another span of sucking all the cock I could find. Often, I’d think it was a shame that I couldn’t be bisexual because my life would be so much better if I could have a woman to live with that would let me suck cock when I felt the need. Eventually I found one but that may be a chapter in itself!
Then I moved to a small town outside of San Antonio, dated local women, and went to Austin or San Antonio when I was in a gay mode or mood or phase. I remarried briefly – it lasted about a year. She was a lot of fun and somewhat accepting of my wearing panties all the time and other ways of crossdressing, like wearing matching bikinis at the coast. It ended when we went to party and she introduced me to a guy that she’d gone to high school with and at the end of the night, he discovered that the guy he’d rode to the party with had hooked up and left him stranded. So my wife told him he could come home with us and sleep on the couch, and we’d drive him home in the morning when we were all much more sober.
When we got home, we kept the party going. Finally, we decided it’s bedtime and discover our fold out couch had lost the mattress somewhere down the line. We’d gotten it second hand and had never tried to fold it out before, so she invited him to sleep with us. When we went to sleep, she was in the middle of the bed and nothing was going on. When she woke up the next morning he was on my side of the bed, feeding me his cock. She freaked out! I’d told her all about my past and that I had a history of sucking cock, might do it again if I had the chance, and she’d still wanted to marry me. Then when I had that chance and took advantage of it, she acted like she didn’t know I’d do that.
She left, filed for divorce and I moved into a new apartment near where I worked. At about the same time I met a couple I’ll call Bob and Ann that lived a block away and frequented the same tavern where I played pool. They had two kids the same age as the kids of one of the women Ann worked with so they set up a sleepover swap where the four kids would spend the weekend at one house or the other giving the other couple some free time. When Bob and Ann were free they’d come to the tavern on Saturday night and one night, while Bob was busy playing shuffleboard, Ann told me she wanted to have sex with me. I told her I considered Bob a friend and that as much as I’d love to have sex with her, I wasn’t going to do it unless he was okay with it. A few minutes later, he came to the table to take a drink from his beer and she told him, “Bob, Alan is spending the night with us.”
So we had a threesome, that night and again the next day. She hadn’t been at all surprised to discover I was wearing panties. She ran the lingerie area of a local Beall’s store and I’d been her customer several times. She told me she never once believed that I was buying things for my girlfriend or wife.
That weekend Bob made the first move, probably inspired by my pretty pink panties, by fondling me when Ann wasn’t watching. Next time Ann walked out of the room, I grabbed his cock and played with it. One time when he was fucking Ann, I stuck my finger up his ass. She was surprised when I ate both mine and Bob’s cum from her fresh fucked pussy but didn’t say anything.
After that night and the next day of MFM sex, things got a little crazier beginning when Bob visited me one evening the following week.
Sometime during our weekend 3-some, talking about sex of course, Ann mentioned that one thing she didn’t like was the magazines that Bob bought and that he’d promised to get rid of but hadn’t and I told her, making a joke of it, that I’d LOVE to solve her problem and take them with me. Ann said I probably wouldn’t like them and when I turned to Bob, he mouthed the word ‘gay’ and grinned.
Bob explained aloud that they were safely stashed up in the attic and without the ladder that had been borrowed by the same people that had the kids that weekend, no one could get to them and especially the kids that weren’t big enough to get out the ladder if it was there. End of discussion.
But a few nights later, Bob showed up at my door with a six-pack and at least 25 gay and bi male fuck magazines that he’d bought from the adult bookstores springing up in Austin and San Antonio. Before we’d finished our first beer, our clothes were coming off and we were mouth to cock for the rest of his visit. I remember that primarily as the night I decided that I did not like to 69. We both loved cock and would rather suck than be sucked so we kept trying to do it at the same time. I didn’t like the distraction. I love to provide oral pleasure to both sexes, and I really get into it, almost Zen like in my focus on orally stimulating the cock or clit I’ve been honored with. Cocks especially get to me in that way, almost mesmerizing in the way I so totally focus.
Anyway, not long after Bob came to see me, Ann called and asked if I’d stop by, Bob was working out of town for three days, she needed to shower, and it wasn’t working right. So I stopped on the way home and she greeted me wearing only a robe that was wide open and when I asked what was wrong with the shower, she said she needed someone to scrub her back.
We continued to have MFM 3-somes but in front of Ann, Bob and I didn’t do anything. Bob knew that Ann and I were getting together but she didn’t know about Bob’s visits and I decided it was silly. She was aware Bob had sex with men in the past and I felt we needed to move to MMF 3-somes.
So the next time that the three of us were together, while I was fucking Ann in the missionary position, I indicated for Bob to feed Ann his cock. While she sucked the head, I began to lick everything that wasn’t in her mouth. Her eyes got huge when he pulled back enough for his cock to slip out of her mouth and I put it in mine and put on a cock sucking show for her right in front of her face. It caused her to have the most incredible orgasm yet, so with that hurdle cleared, Bob and I were open to enjoy sex with each other in our threesome. She didn’t want him to visit me alone, she wanted to be included, but thought it alright to see me by herself, without Bob. I didn’t argue. I was in paradise getting plenty of cock and pussy and getting to dress as Amber
It was wild! Maybe too wild. That same weekend I was fucking Ann in the shower and Bob was fucking me at the same time. I’d never enjoyed being fucked but Bob had a long slender cock that felt great. The problem with doing it in the shower was that we all slipped and fell at the same time, tumbling out of the tub, taking down the shower curtain when Ann tried to grab it for support, and landing in awkward positions on the hard tile floor. It was a miracle nothing was broken – just a few scrapes, scratches, and multiple bruises.
The bottom line from my experience with Bob and Ann, beginning with that moment when I was fucking Ann and sucking Bob, was to decide the guy that wrote the article about there being no such thing as bisexual was full of shit! I knew at that moment that I’d never be able to give up either one.



It was fun while it lasted, but after a year or two, I had to move back to San Antonio to take a new job in the Medical Center and I went back to school at nights which limited my extracurricular activity of any kind to a few hours on weekends. I’d also taken a pay cut to move my life in a new direction, but I was really interested in biotechnology and considered it all to be in my best interest.
We used to joke about getting paid monthly, and it was weakly. The sad part was it was true and I was broke. I’d also screwed up my move.
I’d told my landlord I’d be moving at the end of the month. Then I made a few trips to San Antonio to find an apartment and got lucky there. But that required a deposit and first month rent. I had my own furniture and a buddy had a truck. Between the truck and my car, we were able to get all the big pieces of furniture and some clothing and boxes in one load and I told my landlord I’d be back for my stuff that wouldn’t fit. I was sure I could get it in my car but when I got back, he’d thrown it out. His excuse was that I’d said it was MY stuff and he’d looked in the boxes and it looked to him like it was all women’s things so it couldn’t have been mine. His brother was a city cop or I’d have knocked his lying teeth out. He also had a check to refund my deposit in his hand and I really needed that money.
So most of my lingerie was gone and when I finally got my first check at the end of the next month, I had a lot of things to replace. I needed more panties, and at least one more nightie and some hose. I worked out a budget as to how much I could spend each month and it looked as if it would take me six months and that was if I didn’t get a phone.
Bright and early Saturday morning, after cashing my check, I went to the closest discount store, a Woolco. Close to the front door was the cosmetics area and while I’d have loved to fill the basket, I settled for one bottle of nail polish and two lipsticks and then noticed a hose display. While looking at the hose, hoping to find taupe with a seam, this guy walks up behind me and asks if I’m finding everything I need.
One look at the guy and I was sure he was a store detective. He was big. I told him I was fine and rushed off with my cart to the lingerie dept. I found a table full of panties at 99 cents and then spotted a rack of Valentine’s themed items being closed out. Right in front was a really cute babydoll pajama – my favorite style. Then I spotted another gown in the regular display that I liked. I was looking at bras when I spotted those, did some quick math in my head and decided just maybe I could add a bra or nightgown. So with the bra in one hand I pulled out the nightie, when the store detective snuck up on me again and asked if I needed help.
To me he looked like a NFL lineman and about as far from being a sales clerk in the lingerie department as you could imagine. I decided to go check out and then remembered I’d never gotten any hose. So I doubled back there. The nail polish bottle and lip sticks kept falling through the bottom of the basket so I’d put them in the pocket of my windbreaker and the store detective had made me so nervous I’d forgotten about them. I checked out and headed to my next stop.
A nearby bar had been my hangout after my divorce so I decided a stop there had to be in the budget just to see if any of the old gang was around. It had changed names and when I got inside, they’d done some serious remodeling and while there was no one else in the place, the woman behind the bar was an old friend. Jo Ann had known I was a crossdresser, so I decided to take off the windbreaker, that if she noticed I was wearing a blouse and had a bra on under it, she’d treat it like business as usual. That’s when I discovered the lipstick and nail polish I hadn’t paid for in the pocket and no sooner had I done that than the store detective came in the side door.
I panicked! I’d shoplifted from the store, unintentional or not, and he was there to arrest me! I decided to go in the restroom and flush the stuff down the toilet. Once in the restroom I calmed down a bit and let my mind work.
Just before I’d stepped into the restroom, I’d heard Jo Ann call him by name, ask, “The usual?” and they’d started chatting. It was all just a coincidence.
When I went back out, the guy had taken the seat next to me at the bar. The whole place is empty except for JoAnn and the two of us and he picked a seat next to me. Mmm. When I sat down, he bought me a drink and we began talking.
John was not the store detective. He was the store manager and he had played football in high school, had been offered a scholarship at UT, and had gotten injured in his first practice scrimmage. With all that kind of stuff out of the way, he explained that he’d learned to tell when a guy was shopping for himself or really buying something for his wife or girlfriend. He told me that guys like me, that liked to wear lingerie and women’s clothing, bought cute nightgowns and panties and such after the gifting holidays when it was on sale. If I’d been buying for my wife or girlfriend I’d have bought just one or two items before the holiday, which in this case had been Valentine’s Day.
He kept refilling my glass for me and when he was sure I was feeling it, got to the point. Did I like to suck cock?
I dropped my hand in his lap and told him, “Let’s go!”
He laughed, said he had to get back to work, but would call me, give me time to look pretty, and meet me later. I explained I’d just moved back to town and didn’t have a phone and it wasn’t in my budget right away. I explained where I lived and told him to come by after work and I’d be wearing that sexy nightgown I’d just bought.
He did and that was the beginning. He showed up that night with the bra and nightgown I’d been looking at and had put back. He had a phone put in for me and I got a pocket pager so that we could meet for lunch 2-3 times a week. Every time we met, he brought me lingerie. His store was one of many in a cluster around a big shopping mall and they’d formed an association to pool their marketing efforts in the form of monthly flyers and entertainment events. Because of that, he’d become friends with the woman that owned and ran the Merle Norman franchise in the mall. He arranged for my first makeover complete with a wig. John wanted to ‘date’ me and wanted me to look fully as a woman. He was part of a ‘poker’ group that seldom met. The manager of the Woolco on the other side of town was running around on his wife too and they used a weekly poker night as their excuse. There were four in the group, all supposed to be playing poker on Thursday night. Once a month they’d actually have a game at the home of one of the guys. Eventually he explained that in his mind he wasn’t cheating on his wife if the woman he was seeing wasn’t really a woman. I was providing for him the kinds of sex his wife wouldn’t – oral and anal and it was that anal part I didn’t like. His cock was as big as the rest of him.
He told me I just needed to work at it and one of the first places he took me to was an ABS to buy dildos and butt plugs of assorted sizes that I was to use to stretch myself to accommodate him. He had a solution for every problem which I assumed was why they’d made him a store manager.
I was okay with the noontime quickie blow jobs (one time going back to work with cum on my breath got a reaction from a lady I worked with), and his stopping by after he closed the store for sex was okay too, but it was the date nights on Thursday when he had to leave that I didn’t like. I had fantasies of waking him with my mouth sucking that big, beautiful cock I’d come to love. We discussed it and came up with a plan and it worked.
The guys in the poker night scam had all been careful not to let their wives know much about the other guys and definitely not to let the wives get to know each other. It would have brought the whole thing down if John told Carolyn, his wife, that we’d been at Pete’s place and she talks to Pete’s wife and finds out they weren’t really there. However we decided to make an exception in my case.
John told Carolyn that he felt sorry for me, that I lived closer than any of the other guys, wasn’t married, and didn’t have any friends, male or female outside the poker group, and suggested they invite me over for one of their weekend bar-b-cues.
I liked Carolyn immediately and began to almost feel guilty since I was the ‘other woman’ so to speak. Eventually Carolyn gave me the perfect opening. She told me she didn’t mind his poker nights and even the mess they made when it was John’s turn to host, but that she knew we all drank a lot when we played and she worried about him driving home drunk.
Like I’d suddenly come up with the idea, I told them my perfect solution that should please all the wives and especially Carolyn; that we should hold all the games at my apartment, that there was plenty of room, and that John was welcome to crash on my couch, that I had to be up early the next morning and would wake him in plenty of time for him to drive home, change clothes, and get to work. She thought it was a great idea and I had to hide an erection just thinking about the coming Thursday night.
Those overnight stays were incredible. No matter how late we’d quit the night before you can be sure I was awake early enough the next morning to enjoy John’s morning wood. The only possible way it could have been better would have been if we could have been honest with Carolyn. She didn’t like sucking cock and I loved it. She didn’t like anal sex and I could accept it. She thought sexy lingerie was silly and I loved that kind of silliness. Best of all, I was no threat to their marriage.
The next six months or so were a beautiful time of my life. The woman I would soon meet insisted that I was John’s mistress but since he didn’t pay my rent, I didn’t think so. However in a lot of ways, I guess we were pretty close to that kind of relationship. When he told me he was moving I cried like a baby.
This was back at a time when Wal-Mart was expanding into small cities in Texas, Oklahoma, Louisiana, and Kansas. They made John an offer he couldn’t refuse and I was left without a lover and best friend and as so often happens, as one door closes, another opens.
Had John still been in my life that summer, I might have not started going back to the bar where I watched Cowboys’ games and where I would meet the woman that brought out Amber like never before.

Part 3
The rest of puberty was a mixed bag of very little intercourse but a honing of the fetishes I’d developed going back to infancy. It certainly wasn’t what I expected the morning I’d walked home after fucking Betty.
I’d become a real man – in my mind at least - not only did I have a full bush of hair around my dick, I’d fucked a girl! I’d be a sophomore in high school in a couple of weeks and Betty would be a senior. She’d already promised that she’d introduce me and Bobby to the cool kids which would be a huge help socially. I would be sixteen in a couple of months and would be getting my driver’s license. I had a part-time job promised me, replacing another boy that was going off to college. All in all, I had every reason to believe that I was going to be the biggest stud to ever hit Middlefield High School.
When I explained all that to my little sister, she was happy for me and hoped for the best. Years later she told me she didn’t think I’d be able to give up my sissy side, that it looked to her like that was the real me, and the ‘big stud’ character was more my imagination. My sister was wise beyond her years and fifty years later we both laughed about it. What is important to this story is that the next five years set in motion the fifty that followed.

My sophomore year was devastating. The school year had barely started when the Col. learned he’d be getting his flag and a new job at the Pentagon. Delphene was dispatched to Washington to find them a house and the two kids were left to console each other. Betty was in tears and a blowjob wasn’t enough to cheer up Bobby. That blowjob was the first in a few months and the last one I did for five years. I use those two blowjobs, five years apart as bookends for this period.
Unbeknownst to Bobby and Betty, Delphene had been to Middlefield and gotten most of the school records she needed. When she returned in a couple of weeks, she’d bought them a house (from the Polaroid pictures she’d taken it looked more like a horse farm to me) and had enrolled them in Annandale High School. She and the kids went to work packing and I tried to help but no one was in a very happy mood. The moving van showed up on Friday and on Saturday the Col. moved into a BOQ at the airfield and Delphene, Betty, and Bobby boarded a plane for Washington, D.C. It was the last I saw of them and by Christmas we’d quit writing.
Kevin, thinking only of himself, had tried to convince Betty that since she was 18 she didn’t need to go, that she could live with Susan and stay for her senior year. When Delphene got wind of that, she took Kevin out in the back yard and according to Bobby, he left red faced and without saying goodbye to anyone. A few weeks later I saw Susan at school and asked what was wrong with Kevin’s car since it had been parked beside their garage for a while and found out Kevin had joined the Navy. So there went my last chance of having a cock to suck.
Could I really just quit? Well, it wasn’t like I had a lot of choice. I had a few new friends but it didn’t look to me like any of them had any inclination to fool around sexually with another guy and considering the homophobic remarks that most of them made, I wasn’t about to ask. And I was probably wrong.
I’d love to be that age again and know what I know now. Those guys like me, most likely to make those homophobic remarks, were that way because they’d enjoyed similar experiences in their early teens. After talking to many guys about those years and reading the accounts of hundreds of others, many young men had a blow buddy during Jr. High School or Middle School as it’s called now. So on the slim chance that somehow a rumor might have been started about our fooling around with another boy, we needed to convince each other (and maybe ourselves) how detestable we thought it was to be one of those queers. Had we been honest with each other, there’d have been no need for any of us to go home with blue-balls after our Saturday night dates.
I never got to fuck a girl or suck a cock the whole time I was in high school. But that doesn’t mean I didn’t have my own kinky sort of sex life and two weeks after graduation, a girl I’d dated several times and wouldn’t so much as allow me to take my cock out, almost raped me. Her, “I’m a virgin and I’m saving it for my husband,” story evaporated as soon as high school was behind us. She said she’d really been afraid that being sexually active would ruin her reputation (which I knew to be true) and she was pretty enough that she got a date every weekend without it. Now she was going off to college, had convinced her mom that she needed to be on the new birth control pills ‘to regulate her period’ and didn’t want to show up at the University with no sexual experience. She’d heard rumors about my backstage activity and wanted to know if it was true. So I devoted the summer to helping her as much as possible.
Now about those backstage activities . . .
In my first semester of high school, I took a speech class. My teacher suggested that I take a drama class the next semester, and that I apply to join the stage crew the following year. I did with no expectation of the fringe benefits that would give me and that came about because I played peeping-tom one night at the beginning of my junior year.
It was common for the girls to have a slumber party on a Friday or Saturday night and boys were allowed to visit until some predetermined time. As I recall I had to have my date delivered by ten. We got there early as did some other couples and the guys were sent out at ten and the doors locked. However my date, who I’ll call Sally, told me the host Suzie, had a pool and the girls had all been joking about going skinny-dipping in the pool after lights out.
The house was a nice, older home. In back there was a garage and what had been a servant’s quarters. The quarters had been refurbished for Suzie’s widowed grandmother and that included, in those pre-cable days, the installation of a rooftop TV antenna. That antenna installation had been done a few weeks earlier by me as part of my after school job in a radio-TV shop and I already knew about the pool and the excellent view of it from the roof of the garage.
In the time between my arriving with my date, and the boys being sent home, I spoke with Suzie’s mom and asked if her mom was happy with the TV reception and learned that granny and Suzie’s dad had chosen to escape for the weekend to close up the home where granny had been living. So at 10 pm all us guys were run out and at 11 pm I was in position on the garage roof.
It sounded to me like most of the girls were out at the pool. I would have had to be on the other side of the roof crest and standing to see down to where the girls were gathered and they could have easily seen me, even with all the lights out. However I could hear them with no problem and I got an earful.
I was stunned. When I’d been with Betty and Susan talking about sex, I was sure they were so explicit just to embarrass me. Not only did these girls talk about sex just like the guys did, but they seemed to be much more explicit. When they started talking – almost bragging – about how far each of them had gone with a boy, and they all admitted that at some time they’d all managed to fondle a hard cock and how easy it was to make a boy squirt and how they all wanted to do more but were afraid about ruining their reputation. They covered every base and did it graphically.
By the time Suzie’s mom called the girls inside I’d learned a lot but had no idea how to use it, however I was sure that if I thought about it I could find a way. And thinking about it, almost continuously, had me jacking off night and day.
Then fate played another hand. Had I not installed a TV antenna for Suzie’s parents, I’d have never known how easy it was to get on the garage roof without a ladder, and if I hadn’t been on that garage roof I’d have never heard the girls speculate on the possible pleasure they might receive from having a boy lick their pussies. The one that had done the most speculating and shown the most interest was Patty Marsh and if I hadn’t accepted an invitation to join the stage crew, and she hadn’t accepted an invitation to become the new wardrobe manager for the drama department, we’d have never been working together backstage, usually by ourselves.
We both had a pretty sweet deal – an exemption of sorts. There were six class periods and almost everyone took an English, history, science, and math class with one elective and either gym or study hall. Her sewing/wardrobe class was the same period as my shop/stagecraft class and for reasons that had nothing to do with academics, we kept that schedule through to graduation.
It took a hint here and another there, but by Thanksgiving Patty was aware that I had much more than the normal interest in girl’s clothing and lingerie in particular. I remember that it was somewhere between Thanksgiving and Christmas that our conversations turned to sex and quickly became as explicit as the one’s I’d heard at that summer slumber party and as soon as I could mention it without being too obvious – as I recall it was just after the Christmas holidays, I let her know that I was more interested in oral sex and pleasuring a girl that way. That perked up her interest and she asked, “Really?” but before I could answer two of the other students, both female, came in wanting to use the toilet so I had to step out.
There were two large dressing rooms and only the girl’s had a lock on the door so it doubled as the wardrobe storage room as well as where we kept some of the more expensive audio equipment. In addition, the wardrobe racks were two tiers of pipe, one above the other and the top row couldn’t be reached without a ladder. This was in chivalrous 1960 and girls weren’t allowed to climb ladders so Patty needed me to get things down or hang things up. Boys weren’t supposed to go in the girl’s dressing room but I got an exemption because I worked with Patty and as long as I left the room if a girl needed to use the toilet, no one said anything.
When the two that had interrupted our conversation had finished their business, I was eager to get back to it but knew I had to let her bring it up and she didn’t; I segued into it a few weeks later. However the very next day she did bring up another all-time favorite subject – panties! And the way that played out convinced her I wasn’t one of the “kiss and tell” kind of guys.
Patty was into roller skating on way more than a “something to do on date night” basis. As I recall there weren’t any athletic activities for females at the time. There may have been girls’ basketball and volleyball but if there were games against other schools it was a well-kept secret. I was always ready to do anything for a laugh so when I got on skates people that knew me thought my antics were my attempts at comedy. They weren’t. I was really that bad. On the other hand, Patty won solo competitions and had a partner from another school that won as couples. I had no idea she was that good until I saw all the trophies and ribbons and pictures in her den and bedroom, but I’m getting ahead of myself there.
The backstage area was kept clear and the main curtain dropped and closed most of the time so it wasn’t unusual for Patty to put on her skates and practice something. She had these cute little outfits she’d put on with short skirts and a matching zip-up panty that covered her regular panty. One day I watched her do her routine and mentioned later that her panty cover hadn’t completely covered her panties and it looked to me like the panties were a lot prettier than the cover. That had led to panties being open to discuss or at least make remarks about – enough for her to figure out I had much more than an average interest in ladies’ lingerie.
My ‘coming out’ as a panty boy occurred the day following my confession that I would rather go down on a girl than have regular sex. Patty was going to change into one of her skating outfits and I heard her mumble a curse word or two and asked what was wrong.
The panty cover for her outfit wasn’t in her gym bag with the rest of her things. Our conversations had grown to where she didn’t hesitate to tell me that the last time she’d worn that outfit her period had started early, and the panties and panty cover had both been stained and her mom had taken them to soak in peroxide and wash and they hadn’t been put back in the bag. I told her not to sweat it, that there was just the two of us, the curtain was down, and I wasn’t likely to run down the hall telling everyone that, “Patty’s wearing pink panties.”
She agreed I didn’t seem like the kind to do something like that, but hesitated, then laughed, and told me if I was interested, she was wearing white panties.
I remember the outfit was a beautiful light blue and thinking at the time that the “Monday” panties in the set from a few years back had been the same color blue. So without a thought I told her that if I still had the panties that matched her outfit I’d be happy to loan them to her, but unfortunately, my “blue Monday” panties had been chewed up by my dog.
She started laughing and told me that she thought dogs only chewed up homework, we both laughed about that, and then suddenly we’re having a serious conversation about panties, and I told her a short version of my whole story; letting her know that I still liked to wear them and making her swear she’d never tell anyone that secret. Over the next couple of weeks, we seemed to talk about panties in some way every day. There was a few of those ‘day of the week’ panties still in decent shape and I wore one to school to prove I hadn’t been lying. She teased me about blaming the dog when the others in the set had been destroyed by my ‘playing’ in them, and she admitted that ‘some girls’ like to rub themselves through their panties.
Then in questions about details, I told her how my fascination with Betty’s panties and getting caught sniffing them had led to her letting me sniff them while she wore them and licking them while she wore them, and then licking her almost weekly. At last we were back to talking about eating pussy! Turned out she’d been looking for a way to bring it up again too.
During this same period she had been telling me more about her skating partner, “Alfred,” who liked to be called “Allie” and one story really caught my attention. She told me that Allie usually wore tights and a leotard when they practiced and how Allie would get an erection that made the girls giggle and that the dance instructor had taken him and his mom aside and suggested that Allie should start wearing a panty-girdle to control his excitement and that Allie had admitted to her that sometimes he liked to wear panties too.
Suddenly I remembered those poolside confessions I’d overheard had always been prefaced with ‘a boy at camp’ or ‘a boy where we used to live’ or something of that nature; I couldn’t recall any that had involved their current boyfriends or a guy at our school. She’d told me that she could never have the same conversations with RT that she had with me and that he’d probably want to kill me if he knew about all the things we talked about.
RT in this case was the nickname for her boyfriend, Ronnie Turner, who’d picked up the nickname because his Jr. School football coach had him play Right Tackle and it matched his initials so the kids had started calling him RT and it had stuck. RT was still his initials but he was currently the first string Center and easily made two of me. Keep in mind that this was at a time when obesity was not as common as it is today. RT was almost all muscle, was all-state his senior year, got a full-ride scholarship and played professionally a few years later..
Conversely, I was six foot of skin and bones with one of the highest IQ scores in the school and about as much common sense as a baby goat or I would have never gotten into any of those conversations with Patty. It’s been apparent on many occasions in my life that the innate instinct for survival that we’re all supposed to have was completely missing in me. So when she invited me to her house after school, I went.
Patty made much better grades than I did because she studied and I didn’t. I could grasp what the teacher was telling us, knew they’d talk about what they thought was important, and left it to us to figure out the rest doing homework. I never did homework. When school was over my books went in the back seat of my car and that was it. I was a “C” student at best, constantly hounded for not applying myself. Why she thought I could help her with Chemistry was beyond me, but I didn’t argue.
Her problem, as it turned out, was that she’d been confused since day one about electron theory. She’d never thought of the parts of an atom in an element as being universal. To her, a water molecule was two Hydrogen atoms (blue) and one Oxygen atom (white) and the idea of the blue and white electrons comingling was unacceptable. As luck would have it, I’d noticed a house being framed across the street so I made up an analogy using two by four lumber, pointing out that the wood didn’t care where or how it was used. In one place it made an exterior wall and in another a bathroom wall and around the corner on the side street it was becoming a garage wall. It was only after those pieces of wood were all assembled that it became a room and the rooms assembled to become an element – or in this case a 3 bedroom home.
I’d solved her Chemistry problem in less than fifteen minutes, her parents wouldn’t be home for two hours, and I no longer had an excuse to be there. See what I mean about being a genius without a lick of sense? However in retrospect, I’m sure that Chemistry was not the main motive in my invitation to her home. However the possibility that one of the hottest girls in school, going steady with one of the hottest guys in school, would want to do more than talk about sex with a guy like me was beyond incredulous. However starting that day, things began to move quickly.
I was headed for the door, my ‘work’ done, when Patty stopped me and asked if I’d like to see her new skating outfit for a competition she was going to in Dallas. Of course I did a 180 and followed her to her bedroom in the hopes she’d change with me watching. Instead she pulled out a yellow and white, long sleeve leotard, white tights, laid them on the bed, and then held up two panties. One was the matching panties to the outfit and the other was a yellow pair of sexy panties. She grinned and asked which I thought would go better with the outfit.
The yellow panties in no way matched the outfit but of course I told her I liked them best and when she teased me I admitted that I really liked the panties, wished I had some like them, but that the white cover-up panties were really the better choice. She teased me some more, held out the yellow panties, asked if I’d like to have them, and when I reached for them, pulled them back, calling me ‘panty sniffer’ and telling me they hadn’t been worn and I probably wouldn’t like them. Then she disappeared for a minute and came back with some plain white panties, telling me she’d worn them the previous day and gotten them out of the wash hamper, and I could take them home but . . . only if I wore them to school the next day.
I did. Not only to school the next day but to bed that night and when she got that information out of me and asked if I’d “played in them” I admitted to that too.
Patty talked about sex and body parts in an oblique way. She would use common words or even anatomical terminology. A cock wasn’t a cock or penis, it was a boys “thingie” or “peepee” and pussy was always, “down there” to her. Male masturbation was “playing” and females “rubbed themselves.” In fact most of the girls were the same way. They’d be more explicit talking among themselves, but even my wife, when I married several years later, seldom used common terms.
Patty had skating practice a couple of times a week, and I’d been working after school and full time in the summer for over a year. I could get away with calling at the last minute to say I had to stay at school for some reason but couldn’t do it often, so it was at least a week and maybe more before my next afternoon at Patty’s house and somewhere during that time, Ellen got involved – if she wasn’t already.
Ellen was Patty’s BFF as it’s called today. She was also my lab partner in Chemistry and Patty had the same Chemistry teacher but at a different period. Ellen understood the whole Chemistry thing as well as I did which was one of the reason’s I’d doubted my homework help, which could as easily been done backstage when we supposedly studied together, was the full story. It would have been more logical for Patty to ask Ellen to help her.
In addition, everything I discussed with Patty was supposed to be our secret. We had a “What happens backstage, stays backstage” agreement before the Vegas promoters thought of it. I was hoping Patty meant it because over the semester and Christmas Holidays I’d told Patty everything I’d done, including my time sucking Bobby and Kevin and eating Kevin’s cum from Betty after he’d fucked her. Almost from the beginning Ellen would say something to me in Chemistry class where she’d never had much to say before. She began with commenting that she’d heard I had some interesting conversations with Patty and then asking what we talked about.
I’d tell her, “School work and some personal things and she’d have to ask Patty about that.”
Another time she asked if I knew Patty’s dance partner was gay and dressed like a girl and I responded that I didn’t know but that I thought Patty thought he did. When I asked Patty how much she’d been telling Ellen, she denied saying anything about what I’d told her, but added that I shouldn’t worry about it because even if she accidently let something slip, that Ellen wouldn’t say anything. I think the giveaway day was one morning just before the start of school I saw Patty in a pretty blue dress and I was wearing a blue shirt. I commented that we were matched for the day and that I had on blue panties. She laughed and told me she did too. Later in English class Ellen asked me if I thought she looked sad. When I told her I didn’t think so, she said she was feeling blue and that blue seemed to be the color for the day. From the smile she was holding back I was sure she didn’t mean my shirt.
Later that day backstage, I told Patty what had happened and she told me not to worry about it, that she and Ellen knew everything about each other and she’d never say anything to anyone. Patty asked me how many pairs of panties did I have and what colors. I told her and then she gave me a list of her panty inventory and told me I needed to get some that were lavender, another pink, and one more red and we could wear matching panties and no one would know. I thought she was joking until I got a call early the next morning telling me that the color of the day was pink. Ellen was always giving me this sly smile like she knew my secrets and if she knew for sure we sometimes wore matching color panties then she probably knew a lot more of the things I’d told Patty

So I wasn’t really surprised that the next time I went to Patty’s house, Ellen was already there.
My first reaction was to be upset since I was sure nothing was going to happen with Ellen there. My concern diminished when Ellen asked if we were wearing matching color panties that day.
“Red”, I told her and Patty smiled and nodded in agreement..
“Me too,” Ellen told me with that sly grin of hers. “Patty told me what you’ve been doing. She and I used to do that when we first met in 8th grade. It’s kind of cool to do it again with a boy doing it too.”
“Did y’all wear matching color bras too?”
“Probably,” Patty said. “All of mine were white then and I think all of Ellen’s were too.”
Ellen nodded. “Yeah, still mostly white.”
“The only one I had was white,” I told them. “But it got ruined.”
“The dog again?” Ellen teased.
The only way Ellen could know about my dog chewing up my panties was if Patty really had been telling Ellen everything I told her.
“You tell her everything,” I accused Patty.
Defensively, with her hands on her hips, Patty responded. “Not everything. I never told her you wore diapers.” She realized her mistake as soon as the words were out of her mouth but by then Ellen had fallen back across the bed cackling.
“You have now,” I said to Patty.
When Ellen sat up, I told her, “No not the dog. I put it in with some white things my mom was washing and was going to get it out before she saw it. But she dumped everything from the washer to the dryer without seeing it and by the time I stopped the dryer it was toast.”
“Wait a minute,” Patty told me. “I’ll be right back. Take off your pants and shirt. I’ve got something for you.”
I was embarrassed to be undressing in front of Ellen but she saw me hesitate and told me, “I think she wants us all to be wearing panties and bras,” and she began to unbutton her blouse.
I didn’t know what their plan was but if it involved getting undressed it had to be good. I took off my shirt and shoes and was stepping out of my jeans when Patty came back with a red bra dangling from one hand and gave it to me. “See if this fits,” she told me.
By then Ellen was down to bra and panties and she watched in awe when I put on the bra without any problem and adjusted out the shoulder straps to fit me. Patty smiled and then got a set of falsies out of her dresser.
“Here,” you can keep these. I don’t need them anymore,” she said proudly, sticking her chest out to prove her point.
For the second time in my young life I’d been given a set a falsies by a girl that didn’t need them anymore.
“Now,” Patty told us in a way that we knew we were going to do whatever it was she had in mind from the beginning. “One of you two is a liar.”
Whatever Patty was up to now, it was clear from the expression on Ellen’s face that she hadn’t been told what to expect.
She began with Ellen, telling her, “You told me none of the boys will lick a girl down there and you’d like to have a boy do that. I told you I knew one that would if you really meant it and you said you did.”
Then to me she said, “And you told me all about the girl you used to lick and that it didn’t bother you if she’d already did it with her boyfriend. You also said you love to do it again.”
I could see where she was going and while all of what she’d said had been in an effort to get her to let me eat her pussy, if she was setting me up with Ellen who was even prettier, I wasn’t going to complain.
“So we have a little over an hour to see which of you is lying,” Patty concluded.
“What if he says something,” Ellen asked Patty.
I spoke first. “Why would I say something. If I lick you and you like it, wouldn’t you want me to do it again?” When she nodded, I went on. “And if I said something you’d deny it, everyone would believe you and think I was just bragging, and I’d never get to do you or any other girl, right?”
Again Ellen nodded and that sly smile was coming back. Then I came up with what might have been my greatest idea in my life so far. “The person that seems to have the biggest problem with keeping her mouth shut is Patty. So we all need to be in this together. You both know I like to wear lingerie and that sometimes I wear diapers. If I told anyone and you found out you’d tell them about me and if I happened to be wearing panties that day, it was prove you were right so I wouldn’t dare tell anyone about anything we did. And the only way I can be sure neither of you tells anyone I ate you pussy is if I eat both of you.”
Patty was still fully dressed and may have intended to stay that way and just watch me eat out Ellen. I wasn’t sure if this new wrinkle to the plan would work, but when Ellen jumped in I was sure it would.
“He’s right Patty,” Ellen told her. “You need to be part of this. You told me you want to try it too so if you’re not doing it neither am I.”
Patty was still hesitant so I tried a different angle. “You know how I told you that I began by licking Betty through her panties. Well take off everything but your bra and panties and let’s start there. I’ll do each of your for a few minutes and then you can decide if you want to take off your panties.”
Somewhere in that little speech I’d flipped a switch in Patty’s brain. She went from hesitant to ripping her clothes off in the snap of your fingers.
“Who goes first?” Ellen asked.
“Doesn’t matter to me,” I responded. “I think you’re both super sexy. Who’s oldest?”
“I’m almost two months older than Ellen.”
“Guess you have to do the old lady first,” Ellen chided.
And that’s where I began. I had Patty lie back across the bed next to Ellen and then got between her legs and buried my nose in her slit. One thing Betty had always liked was when I would start by using the bridge of my nose to rub her slit and it was a few years later before I found out what I was doing was rubbing her clit. At that time with Ellen and Patty I’d not even heard of a clitoris. I just knew that the bridge of my nose fit into the top of a girls slit like that’s what it was made for. I also knew that Patty and Ellen must have planned this because it smelled like they’d each used a half bottle of perfume on the crotch of their panties. They didn’t smell natural at all and I was disappointed.
I went back and forth a few times and then while licking the crotch of Ellen’s panties and reached and pulled them to one side and I was able to get my tongue in the folds of her pussy. I heard her say “oh shit that’s good,” but I didn’t know if she was telling me or her friend. When I went to give Patty a turn she’d removed her panties and out of the corner of my eye I saw Ellen was taking hers off too.
I learned something that day. I tried doing the things that Betty had liked and they seemed to work on Patty but not on Ellen. However Ellen was the more vocal of the two and would give me hints of what she wanted more of and with her hands resting on my head, she was sort of steering me at times. There was something else I noticed after a few minutes and that was the girl I was eating would put a hand in the pussy of the other when they thought I wouldn’t notice.
Patty was the one to call an end to it and I rose to my knees to look down on them. They both had dreamy looks on their faces and at some point they’d each pulled their bras up above their tits instead of taking them off. and it was my first look at two beautiful sets of teenage breasts and they laughed when they realized I was staring.
“We want to see you do it,” Ellen said and Patty nodded.
“Do what?” I asked playing dumb. It didn’t surprise me at all. Betty and Susan had asked for the same show.
“Play with yourself until you shoot,” Patty explained.
I knew it would be much of a show. I’d been humping myself against Patty’s bedcover the whole time I’d been eating their pussies and I was sure I knew what they really wanted to see. I’d told Patty about shooting in my hand so I could lick up my cum and it was apparent to me now that anything Patty knew Ellen did too.
“That’s too embarrassing,” I told her.
“Please,” Ellen whined in that little girl begging style that a lot of women use. There was something I liked about hearing them beg.
“Do it like you usually do it,” Patty said, confirming it was the cum eating they wanted to see. “And you can keep the red bra.”
I had no idea where or when I’d have use for a red bra but I liked it and since I’d had every intention of doing it anyway, I fulfilled their request, jacking off into the palm of my hand and licking my hand clean, even over acting about how great the cum tasted.

I doubt there was a single day of the spring semester or my entire senior year that I didn’t wonder if that would be the day the whole world learned of sissy Alan, the guy that liked to lick pussy and eat his cum and dress up like a girl. Patty couldn’t have done a better job of marketing my cunnilingus skills if I’d hired her to do the job but it would seem that the only one she’d shared the whole story with was Ellen. That didn’t last long.
Remember I said that sometimes I can be some combination of dumb, slow, and naïve? Well one night I got a call from Carol, a girl in my history class that hardly talked to me and after beating around the bush for 20 minutes and with her parents hollering ‘time’s up’ in the background, she told me she really called to ask if I’d help her with her chemistry homework. Now you’d think I’d catch on to that instantly but, like the stupid idiot I can be at times, I told her I didn’t realize she was taking chemistry. She was silent for a moment and then in almost a whisper she said, “Patty told me to tell you I needed help with chemistry.”
I think my little head figured it out before my big head did. By the time I realized what she wanted, I already had a hard on.
Three days later, on a Saturday afternoon, we had what I came to think of as “the conversation” because there would be five more almost identical conversations over the next year and a half.
‘If ____ finds out he’ll kill me and you too.” (Fill in the blank for name of current boyfriend.)
“The only way ____ is going to find out is if you tell him. I have no desire to suffer a slow and painful death.”
“I wouldn’t tell him!”
“Unless y’all decide to break up and you want to hurt him.”
“Okay, here,” she’ll say, handing me a pair of panties. “I heard you wear panties all the time and you want a pair of panties from a girl before you’ll do it.”

It wasn’t until an incident with my first wife that I came to realize that it wasn’t just the men that thought pussy stinks, that a lot of the women did too. They couldn’t believe any boy would want to put his face in their crotch without something in exchange. I would have gladly done it without anything in exchange like I’d done for Betty but she had given me panties and a nightgown and knowing that, maybe that’s where Patty got the idea that the girls should be giving up a pair of panties in exchange for getting those pretty little pussies eaten. It was a twist Patty had added and since jacking off in panties had become my entire means of sexual relief, I gladly accepted their offer. What was really nice was that a couple of the girls had gotten the impression that I wanted a pair of panties every time. By graduation, between the ones I’d bought, the ones my sister had given me, and the ones I’d earned eating pussy, I could wear panties every day and go two weeks without washing the soiled ones.
As my high school years came to a close, I reflected on my accomplishments and expectations, and they weren’t even close. In one way I’d had sex and a lot more of it than any of my buddies but I didn’t dare tell any of them what I was doing. The word in the hallway was that Alan was weird but that a lot of the popular girls seemed to like him. My panty fetish became well known among the girls and I’m sure if I’d had to go through another school year the guys would have gotten wind of it too. I’d thought after that great afternoon with Patty and Ellen that one or both of them would want to do a lot more of it, sort of a female version of how Bobby had wanted me to suck him off every day after we started doing that but it didn’t happen. Patty would get me to eat her maybe once a month and Ellen didn’t ask again until after graduation – immediately after graduation. She was my date graduation night and we had real sex, the whole thing with sucking and fucking and eating pussy and it was awesome.
Ellen had been going steady with one of the football heroes as long as I’d known her and for some reason he dumped her about a month before graduation. She called me a week before graduation and I was sure it was for a pussy licking session. Instead she told me she’d heard I didn’t have a date for graduation night and she didn’t either and she’d love for me to be her date. Of course she had to tease me and say something about giving me a pair of panties. I told her it wasn’t necessary and all she needed to do was tell me the color of the day so we’d match. We hadn’t done that in many months so she thought that was cute and I did get a souvenir from that night besides a tassel.
Ellen had been wearing stockings and a garter belt and when we were getting dressed to go home, she gave them to me, telling me she was sure I had plenty of panties but since I’d admired the stockings and garter belt, she wanted me to have them since she’d really liked the surprise I’d given her. That surprise had been going down on her after we’d fucked. I think she’d had an orgasm when I did that. For whatever reason, she gave me a recommendation that led to the greatest summer of my young life.

Of the girls that had joined the “I gotta try that” club, the reaction was mixed, from Kaye, who had been the least enthusiastic, to Wanda, who came back twice and then declared, “If Johnny doesn’t start doing this for me I’m gonna cut him off,” and it must have worked because soon after that they got engaged, to Patty, the one that got me started and seemed to enjoy the conspiracy angle of what we were doing as much as what we were doing. I’d hoped that at least one of them would want to continue after graduation and one did; the one I least expected to hear from.
In my opinion, one of the great things about pleasing a man or woman with oral sex is the ability to watch their facial expressions. Kaye didn’t have any. I’d gotten the impression that she’d been told that sex for pleasure was sinful and she’d decided to try a few things but not enjoy them to keep from sinning. I was pretty close to being right. Even her proposition sounded more like a business deal than a sexual tryst.
I was the effeminate nerd that liked to wear panties and was knowledgeable about sex. She’d given her virginity to Brian at the same graduation party I was at and the word among the girls was that I kept my mouth shut – not that she was concerned about that since she was now out of high school and headed to North Texas on a scholastic scholarship. Her concern was that she’d not know how to please a boy with experience so she wanted me to show her all the things a girl could do and she’d provide me with whatever lingerie I wanted. I almost turned her down.
Not on the sex. No way was I going to miss out on any of that, but by then I’d accumulated several pair of panties, two bras, a garter belt and stockings, and two nightgowns. I was running out of places to hide it, especially the things that were soiled, mostly with cum stains.
I’d acquired another talent that I’d yet to mention and that was working on cars. They were much simpler back then and I’d been at it since the 7th grade, hanging around older boys that were hot rodders, and building my 29A roadster in the back yard, much to the chagrin of my mom. That skill came in handy the day Kaye and I almost got caught.
We were in the living room, just getting started when Kayes dad came home. Like most of the girls, Kaye was forbidden from having a boy in the house if there wasn’t a parent home and with my car out front and the only exits being the front door or out through the garage, I was stuck. Fortunately Kaye was a quick thinker, telling me to go in the kitchen and then greeting her dad as he came through the door.
He didn’t want to hear any of that ‘hi daddy’ shit. He wanted to know who was here and why and she told him I’d looked at her car and I was washing my hands. Taking the hint I turned on the kitchen faucet and was washing my hands when he came in the kitchen.
Kaye had just started driving. She was an only child, and Kaye’s senior year, her mom had decided to join the women that were going back to work. Her mom had gotten a new car and Kaye had gotten her mom’s old car, and her dad had been teaching her to drive. One of the things Kaye was supposed to do that summer was to make sure the car was in perfect condition before she took off on a three-hundred mile trip to her college. She’d asked me to look at it and it did need a brake job and I took her dad out and showed him – had him listen to the grinding noise of the brakes on the drums – and told him as a favor to Kaye, I’d do it for five dollars and parts. Keep in mind that minimum wage was less than a dollar so it was a good deal for me, I had an excuse to go to Kaye’s house, and her dad was happy to save some money.
The first time I licked Kaye’s pussy, she’d been more like a disinterested observer. It had been the only sexual experience she’d had until graduation night when she’d allowed Brian to fuck her and she told me she wasn’t impressed by that either, yet knew there had to be something she was missing since her older cousin bragged about her sex life and how great it was being in college where she had her pick of horny boys and their always stiff dicks. All through school she’d never let a boy play with her tits or rub her pussy or do any serious petting and it had been a dare from her cousin, late in her senior year, that had made her contact the boy she’d heard about that would lick her. She’d also heard that I’d be happy to jack off and lick up my cum but she hadn’t wanted any of that. We’d gotten undressed, she let me lick her for 5-10 minutes, and then got up, thanked me, handed me pair of panties out of her drawer, and sent me on my way.
By that point in my life, I’d become aware of fore play and how important it was so the first time we got together that summer, she was thinking we’d jump right into it and I didn’t. All I did was talk about it, all the things a boy and girl could do, how a boy could use his hands on a girl’s body almost as if he were playing a piano and she was the keyboard and I could see her facial expressions changing. I left without ever touching her physically, but I’d touched her mentally and when I came back a couple of days later, she was a tiger!
Then her period started and she wanted me to teach her how to give a blow job. I wasn’t too happy to discover that she’d heard I’d sucked off boys too and that I loved the taste of cum. I think Patty may have embellished some of the things I’d told her but I wasn’t going to complain or argue. Her cousin had told her that sucking cock was mandatory during your period or the guy you were dating would find someone else for a week and you might not get him back if the other girl was a better fuck.
It was during the two months with Kaye that my mom found my lingerie. I kept promising to clean my room and never got to it so with my sister out of school for the summer, she decided that the two of them would clean my room for me. I came home to find my lingerie spread out on top of my bed and I think the way my mom put it was, “You don’t need any of that any more do you?” I told her I didn’t and that was the last I saw of it. I’d gotten two more pair of panties from Kaye that were still in my car but I seldom wore them. One pair went in the house to masturbate with and the other went in a suitcase in the trunk of my car.
So for me, those visions I’d had the summer before starting high school didn’t come true until the summer after I graduated. As to sex after Kaye, I went to graduate school.
I had a fake ID and in spite of being a 120 lb, six foot scarecrow, I could get into country western bars without a problem and having a celebrity singer for a friend didn’t hurt at all. It was scary at first that older women (at that time mid-20s to me was an older woman) would come on to me. Then the following year the hottest new book on the bookshelf was, “The Graduate,” and it was open season on guys like me that looked like I was sixteen, could dance, and loved to eat pussy. There was one club that had a “Ladies’ Night,” on Thursday nights with a live band and no cover charge for the women. All I had to do to get laid was to be there on a Thursday night. What began to amaze me was how many were married. I didn’t let it bother me.

Then came my trip to California and the sudden re-emergence of Aurelie.

One of those married ladies from the Town Club asked me to drive her home, that she was too drunk and on the way a guy pulled out in front of me. It was his fault but he took off and I couldn’t chase him. I wanted to call the cops but she didn’t want me to. I got the car home for her and I’d had a friend follow me in my car so we decided to wait until the next day and daylight to look at the car again and she didn’t wait. First thing in the morning she had the Ford dealer pick up the car and she had an estimate of over $500. I told her I’d pay the deductable and she told me she didn’t want to tell her insurance company. She asked me to pay all of it, today, so the car would be fixed by the time her husband got back from his trip.
Coincidently, a friend of my dad’s was visiting with him. He’d gotten a great job with Lockheed and was moving. His wife and kids were already out there and he was leaving in the morning with one car and would be flying back to pick up the other one. On the spur of the moment I offered to drive the 2nd car if he’d pay my expenses and fly me back and he loved the idea. So off I went the next morning.
I took all the money I had in the bank plus the money he’d given me for a plane ticket and had a great time in the LA area for a few days. I rented a car and stayed at a fancy hotel and hit all the clubs I’d heard of. When I was down to seven dollars, I couldn’t even buy bus fare so I started hitchhiking home.
I was about 75 miles out of LA when a soldier home on leave from Ft. Hood, Texas, picked me up in his new Chevy Bel Air convertible. At noon we stopped to eat and he bought a six-pack and we were on our third beer when he decided it was too nice a day to have the top up, that there was no one on the road and we should strip to our underwear and get some sun.
The underwear I was wearing was the black lace panties that Kaye had given me that had been in my suitcase for two years. I’d given up that what with all the women in my life I was sure I was straight and had no interest in sex with guys again. I was wearing jeans and a t-shirt and when I’d bent down to pick up some money I’d dropped at lunch, he’d seen the lacy black panties.
When I tried to beg out of taking off my jeans, he told me he’d seen the panties and it was okay with him and not to worry about it, that I wasn’t the first guy he’d met that wore panties. So with two beers in me and most of a third, suddenly I’m riding down Hwy 66 in a convertible and all I’m wearing is panties and all he’s wearing is boxer shorts and we start talking about sex. Next time I glance over at him he’s got his cock sticking out of his shorts, it’s fully hard, and he’s slowly stroking it with one hand. I could take my eyes off it.
“It’s dangerous to drive with one hand at this speed,” he told me. “If you’d stroke my dick for me I could put both hands on the wheel.”
No problem there. I didn’t want to be responsible for us having a wreck.
“I really need to cum but I hate to ruin the new upholstery.”
I knew how to solve that problem. I put his cock in my mouth, the first in five years, and it was every bit as good as I remembered when I’d jacked off thinking about sucking Bobby and Kevin. I didn’t have to suck long before I was rewarded with a big, thick, creamy load. His cock must have twitched and spurted a dozen times. To my delight, the reloads were just as good!
Once I’d sucked him there was no sense in not telling him how I’d learned to do that years back and admit I’d missed it and how I’d enjoyed my high school years eating pussy and getting panties as a reward and when he asked, admitted my ass was still virgin as I’d never tried that. When we got to Flagstaff, he had a plan.
The second time I’d blown him I’d cum in my panties. I’d speculated about the chances of finding a rest stop where I could rinse them out and he’d coupled that need with my stories about earning panties from the girls and my having a virgin ass and told me he wanted to get a room for the night in Flagstaff, and that he’d find a store that sold lingerie and get me some panties and a nightgown. All I had to do in exchange was give up my virgin ass and at the moment that sounded like a great deal.
He found a shopping center with a Sears and a JC Penny store and I’m not sure which he bought my things at. He’d picked out a white gown and matching panties plus a pink pair to panties to wear the next day. He explained that virgins were supposeda to wear white so that’s what I wore to bed. Having had it in my mouth, I knew how big his cock was and it hurt every bit as much as I’d been afraid it would.
He fucked me again the next morning and on the road, when we got to New Mexico, he told me that I should blow him in every state and that way I could brag to my gay friends that I’d sucked a dick in every state I’d traveled through on the way home. He was certain I wasn’t being honest about not having gay friends. I sucked him off one last time in a rest area just before we got to Abilene and then we parted ways.
Not long after that I got my notice to report for my draft physical. I knew a doctor could tell if a woman was still a virgin but I sweated out that physical thinking there might be some tell-tale clue that I’ve had sex with a man.

I thought about that trip almost every night. I’d tell myself it wasn’t ever going to happen again. But then when I’d start jacking off, I’d get out that nightgown and a pair of panties and something to use in my mouth and butt like it was a cock, an have an ejaculation as good or better than the woman I was with at the time. While it continued to be my favorite fantasy, I made no effort to have sex with another man for ten years. Then, like the Army Sgt. It was my lingerie that led to me giving in to my urges.

For the first year or two I was an insatiable cocksucker. I wanted cock. I wanted cum. I wanted it often. It seemed like any time we were together, at his house or mine, and we had an hour of privacy, I’d be wearing lingerie and had his cock in my mouth. If we were playing and needed to pee, having our cocks out was all it took to inspire me to drink his pee and give him a blowjob. Bobby was nearly as bad and then we both got serious crushes on girls at school. In bed, I pretended to be his crush, but since he didn’t want to lick ‘her pussy’ the consensus of opinion among our peers being that it wasn’t a manly thing to do, he felt no obligation to lick my pretend pussy and while I should have been upset about that, I wasn’t. It made me feel more feminine – when it came to sex, he was the man and I was the woman.
As to eating pussy, I didn’t agree at all, but could hardly tell him I’d been licking his sister’s pussy and it was awesome! Looking back I think he was having misgivings about the whole thing but didn’t want to give up getting a blowjob whenever he wanted.
Bobby was a natural athlete, and I was just the opposite. I’d enjoyed baseball but when puberty hit, I had two left feet and five thumbs on each hand. So, during the school year Bobby was often at practice for some sport and I’d be over at his house talking to Betty. If Susan was there, they’d either tease me or ignore me around Delphene. However, if she was gone, I’d get to be one of the girls and they loved to talk about sex. The best times were when both of their parents were gone, and I was staying over at Bobby’s house Friday night and Bobby would have a game or meet the next day. I’d spend the night being his girlfriend and the next day when he was gone, as soon as we’d finished cleaning house, Betty would take me to her room, and I’d get to eat her pussy. If Susan had spent the night, she’d help clean house and then we’d go to Betty’s room, sit on her bed facing each other, and the talk would always turn to sex.
Teasing me, asking me if I’d ever had sex with a girl, or a boy, and if I could, what would I like to do and who would I like to do it with. It was the same questions with the same answers we’d given to each other a week or two or three earlier. I never said anything about having sex with Bobby and every time I’d eaten Betty she’d reminded me of what would happen if I ever said anything to anyone. My crush at school was named Nora and so that’s who I used as the object of fantasies - telling them how if she’d let me I’d be glad to lick her pussy. Betty had never let me forget that I’d once been so stupid as to believe pee made a girl pregnant, that Bobby and I had been peeing on each other, and then they might tease me that the reason I wanted to lick a girl’s pussy was because I liked the taste of pee.
Betty and I had discussed that several times and I’d told her that if it was pee that made her taste so good I’d be happy to drink some but she wouldn’t do it. However in front of Susan, I never said more than that if Nora wanted me to taste her piss I would.
The male object of my fantasies for the girl’s sake was a guy named Hank. I didn’t really have a crush on him but I’d thought a few times that I’d like to try sucking his cock. I don’t remember the reason, other than he’d been a ninth grader taking gym with us 7th graders and MUCH more developed than any of us. He had a man-sized cock and full bush of hair around it. I was always grateful that he never gave me away because more than once he’d caught me staring at it with my tongue hanging out. Both girls knew who he was so they’d get excited when I’d describe his cock and hairy bush and all the things I’d do with it if I was really a girl.
All that talk would make us super horny and with us sitting like we were with our legs crossed we could see the crotch of each other’s panties. It was impossible for me to hide my stiff little dick and of course they’d tease me about that, telling me things like, “Your little pee-pee wants you to play with it.” Masturbation was discussed and they wanted me to show them how I did it. I told them I’d show them if they’d show me how they did it and they always said that girls didn’t do that.
Betty’s tits were big and round with a nipple not any bigger than mine, but Susan’s fascinated me. They were sort of cone shaped with nipples that seemed to have grown bigger every time the light was just right and I got a chance to see them through her nightie. Betty would tease me later about how someday I was going to shoot off in my panties from staring at Susan’s titties.
So I wasn’t completely surprised when one morning while the three of us chatted about sex until they began to tease me about the wet spot in my panties, that all of a sudden Betty tells me that Susan will let me see her tits naked if I’ll jack off for them. I was so quick to get my dick in my hand that I almost shot off before she could get her nightgown off. When I filled my hand with cum they wanted me to swallow it or at least taste it and I refused, telling them that only real girls did that. I’d admitted to Betty that I often did that at home, but wasn’t about to tell Susan I’d become a cum slut.
Then a few months later, under very similar circumstances, Betty was teasing me about something, I stood up to her, and she countered by telling me I was so dumb I didn’t know the difference between piss and cum. I came back with one of the biggest slips of my life. “I do so,” I told them. “They taste different!”
Susan started laughing and bouncing on the bed and told Betty. “See. I told you. He’s been giving Bobby blowjobs!”
I hadn’t really admitted that at all but I must have thought I did because I turned bright red and when I looked at Betty, she was staring me in the eye and said, “You have, haven’t you.”
So I admitted I had but that we’d only tried it a couple of times, making it sound like two times instead of by then possibly two hundred, and to keep him out of any possible trouble, told her Bobby never did me, that I played at being his girlfriend. By then, that was the truth. She told me, “no more,” in a very meaningful way.
If she ever confronted Bobby, I wasn’t sure. He never said anything and I never asked. But within weeks we did slow down drastically and then stopped. Betty had also told me she didn’t want me to be ‘Aurelie’ around Bobby anymore. I didn’t mind blowing Bobby while dressed in boy clothes but neither of us enjoyed it that way. Funny thing though, if the Collin’s parents were gone, and I came over to their house and Bobby had to leave, Betty would ask me if I’d like to dress like Aurelie and spend the day with her and that always lead to me with my tongue licking on her sweet pussy.
And that led to how I got my first fuck.
What I wasn’t aware of was that Betty had developed a crush on Susan’s brother Kevin, the guy that had been a mentor for Bobby and me and he had the hots for her too and for his own sister as well. I later learned that Kevin had been trying to talk Susan into giving him a blowjob and in anger or exasperation or for whatever reason, she told him that if he wanted a blowjob so bad he should ask me, that I’d been dressing up like a girl to suck Bobby’s cock and Betty had made me stop so I probably needed to find a new cock to suck.
I was totally oblivious to any of that so one day when I was several blocks from home and Kevin pulled up and offered me a ride, I jumped in his car. And when we got to his house and he said no one was home and asked if I’d like to come in and have a beer – actually what he cunningly asked was if I was big enough to drink beer – of course I said I drank beer all the time.
He brought each of us one and a few Playboy magazines of his dad’s. I was so clueless that I didn’t realize I was being seduced. Even when he moved to stand next to me and said to feel how hard he was getting, I just reached, squeezed his stiff prick through his jeans and went back to looking at the pictures in the magazine.
I was halfway through with my second can of beer when he told me that he knew all about what I’d been doing with Bobby, that he wanted me to dress in some of Susan’s clothes, and that if I didn’t blow him he’d tell my parents what I’d been doing.
Talk about mixed emotions, I had them. I wanted to dress in Susan’s things and I wanted to suck his cock. I’d often thought of how impressed I’d been when years earlier he’d jacked off and shot what had looked to me like a quart of cum. I’d been thinking about giving his cock another squeeze, maybe even ask to see it, when he’d stopped me by telling me he knew about me and Bobby. If he’d stopped there or just asked me to blow him I’d have gladly done it. In fact if he hadn’t asked I’m almost certain I would have offered. But then he threatened me and I didn’t like it at all. But I did it.
He brought me some panties and one of Susan’s slips and made me wear lipstick and I sucked him off twice before I went home. A few days later he called me and said he was home alone and I’d better come over and blow him again. Like before, if he’d have asked, I’d have been happy to do it, but he had to threaten me and I don’t know of anyone that enjoys being blackmailed. Even after I told him all he had to do was ask he still felt compelled to use coercion.
Just so you don’t get the impression that I was a poor, innocent victim, I never once tried to give him the impression that I didn’t like what I was doing, and I remember one instance where I initiated it in a way. I saw Susan going to Betty’s house and knew that both their parents worked. I also knew that Delphene was taking Betty shopping for school clothes so Susan must plan to go along. That meant Kevin was home alone for a couple of hours so I called him, told him someone had been calling our house and they hung up before I could get to the phone and I wanted to make sure it wasn’t him trying to get me to be girly for him. Of course he told me that was a great idea, that Susan was gone somewhere with Betty and I’d better get my sissy ass down to his house ASAP or else.
I guess I’d sucked him off maybe eight times in a month, often twice each time and then he called me at home late one night when everyone at my house was getting ready for bed. He told me I had to sneak out of the house and spend the night with him or else. My folks never realized I wasn’t there in the morning so I got away with it and truth be told, I loved the way he cuddled me in his arms and having access to his cock any time I wanted it. But I also realized that what he was enjoying as much as my ‘pussyface’ as he so lovingly called it, was the power aspect of it and it would keep building, with him making me do riskier and wilder things.
So I went to the only person I knew I could trust – Betty. She knew Susan had ratted me out to Kevin but didn’t know Kevin had followed up. She picked up the phone, got Kevin on the line and told him she wanted to see him as soon as he could get there. He assumed he was going to get laid and was at her door in just a few minutes. But he wasn’t so happy to see me sitting there when he walked in.
Betty took over instantly, telling him to sit down and shut up if he didn’t want to go to prison. She told him that I was fifteen, he was nineteen, and that he was guilty of statutory rape of a minor, that if he’d been dumb enough to tell my parents anything, they’d have called the cops and he’d spend a few years in jail. Kevin left a much meeker young man than I’d ever seen him act before.
For a while, things went back to the new normal which meant that the only time I got to be Aurelie was maybe once a month with Betty or by myself at home jacking off. To make things worse in my opinion, Betty had started dating Kevin again and I was pretty sure they were having sex, but that didn’t stop her from asking me to visit on the side. I didn’t like that she’d talk about Kevin while I was with her, but in a way, it was good for my ego.
She was three years older, about to be a senior, and asking me questions about sex. True they were questions about how to suck a cock and what things did Kevin like me to do, but I also knew from things he’d said that he would have never eaten her pussy and she’d gotten to really like it. So in a weird sort of way, I was proud that I could do things older boys wouldn’t and could teach older girls the best way to make their boyfriends happy.
This was years before the term ‘cream-pie’ was being used but it had been on my mind for over a year, since one of those slumber party type sessions with the two girls asking me questions. Susan had started hitting me with a bunch of, “Would you . . .,” type questions about different sex acts and she’d segued from, “fuck a girl” to “eat her before you fuck her” to “eat her after you fuck her” and when I’d said yes to all of them, they’d wanted me to confirm that I’d really eat out a girl that had been fucked.
So when I became certain Kevin was fucking Betty, one afternoon while I was eating her I asked if she’d let me eat her after Kevin had fucked her. She got mad for some reason – probably that I’d figured out what was going on between them - and then told me that Kevin usually pulled out or wore a rubber.
It was a week or a month after that when I spotted Kevin’s car in front of the Collin’s house and knew that Bobby was with his dad and mom at a college football game. So I let myself in the house and went to the bathroom to put on my nightgown. It was a Saturday morning and I was going to use the excuse that I was there to help her clean house. Kevin knew I’d been doing that so it was weak, put a plausible excuse. There was a hook on the back of the bathroom door in the hall and Betty always left two or three nighties hanging there. One had been designated as mine. I’d stripped to my panties and had just gotten the nightie over my head when I heard them come down the hall, his telling her good bye, and then the bathroom door flew open and there’s Betty, completely naked.
I just stood there staring at her with my mouth hanging open. In all the time I’d known Bobby and Betty, and the things she and I had done, she’d never been completely naked. I’d seen every square inch of her body, but never all at once. I’d seen her in a robe gapped open, or wearing just a pair of panties, or in bra and panties, and in just a babydoll top with her pussy bare when I ate her, but never had I seen any real, live girl completely naked except my little sister when we’d been much younger.
She told me to get out of her way, she needed to douche and I knew that had to mean Kevin had just cum in her so I offered to lick it out and she hesitated for a second and then grabbed me by the arm to pull me into her bedroom and into place between her legs.
That first cream-pie was delicious and I was close to cumming myself as I ate it. What I later discovered was that while Kevin had a nice cock, he didn’t have a clue how to use it and would cum after just a few strokes in and out. I knew that when I’d sucked him he’d cum much quicker than Bobby usually did but I attributed that to my cocksucking skills. Nope, he was just quick on the trigger and had left Betty hanging.
A few times in the last year I sensed that Betty was close to having an orgasm when I ate her. She’d explained to me what she knew about the whole orgasm thing but it was still pretty much a mystery to me since there didn’t seem to be any way for a guy to know if a woman really had one. When a guy cums there’s that delicious white cream to prove it, but with girls you had to take their word for it. Betty had been getting much more vocal when I ate her since she’d been fucking Kevin and this time, with me eating her right after Kevin fucked her, it was a good thing that no one else was in the house.
All of a sudden she’s muttering, and cursing and then screaming, “FUCK ME, FUCK ME,” and I thought she was giving me orders, like when she told me how she wanted me to lick her. So before she could change her mind (or figure out what I was up to), I had my panties down, my nightie pulled up, and my cock in her. At first she’s saying, “No, no,” and then about the time I’m about to stop because she’s telling me no, she’s going, “Yes, yes,” and she’s screeching and clawing up the back of my nightie. I have every reason to believe that my first fuck was her first orgasm, but I never asked.
I’d already decided as I was fucking her that I wanted to eat her some more after I’d added my cum to the mix, but I never got to. As soon as she realized I’d cum, and before I could get out of her way, she flipped me off of her and onto the floor between the wall and her bed. She’d rushed to the bathroom to perform the douche I’d interrupted and now with a greater need than ever. As she later explained, Kevin had been in the process of pulling out when he’d cum and his load wasn’t deep at all. In fact she hadn't been certain if he’d gotten any in her or not and that’s why she’d allowed me to eat her. I’d gotten most of it with my tongue with no problem. However mine was as deep as I could thrust and if she got pregnant, it would have been my baby she’d be carrying. Kevin’s baby she might explain but not mine.
So again I had a lot of mixed emotions that afternoon. At the top of the list was the loss of my virginity! I’d become a real man but . . . who could I tell? Certainly not Bobby who would have killed me if he knew I’d fucked his sister. Tell Kevin? If I did that, Bobby would have to stand in line and all he could hope for was a chance to kick my corpse. There was only one person I could possibly tell and that was my little sister.
She knew her big brother was a closet sissy. There were times our relationship was like I was her big sister instead of big brother. She knew I liked to wear panties whenever I could, and sometimes slept in a nightgown. Our parents would never walk in our rooms without knocking but she and I had a more open agreement. She had once walked in on Bobby and I and I’d had his cock in my hand, inches from my mouth and would have been sucking it had not Bobby spotted her and jerked back. Later she’d confirmed her suspicion by telling me, “You were gonna put his pee-pee in your mouth, weren’t you?” and I’d smiled and admitted that I was and she’d never said anything else about it. From then on, whenever Bobby came over and she saw me in a nightgown when he left, she had to know why but never commented. Because of that, I felt I owed it to her to let her know her big brother liked sex with girls too and she was happy for me. I think she thought I was going to give up my sissy activities and I probably thought the same thing.
We were both wrong to some extent.
For me this would be the second time that I was sure I’d be putting all that sissy stuff behind me. When we’d moved to Texas had been the first with giving up diapers and panties and sleeping in nightgowns.
Then three years later, after going to the last day of school as Aurelie, I’d gotten right back into it and during the last three years I’d added a taste for cock and cum. Would I or could I give that up? I was sure I could since I was now the big stud.
Funny thing though, I never once thought about throwing out Aurelie’s collection of girl’s panties and other things, and I still had the cloth diapers and rubber pants that I’d been wearing and wetting from time to time. Why was I hanging on to that?

Chapter Two
Bumbling through Puberty
Part One – First Blowjob


I’ve tried to recreate this phase of my life as accurately as possible but it was a long time ago and I could be off a year, plus or minus, because I’m not really sure. When I read back over it, I think I’ve got something out of order and change it only to come back a week or a month later to change it back. What I do know for sure is that all this happened in a period of just over three years, from the end of the 6th grade to some time in my sophomore year of high school.

I remember my first blowjob like it was yesterday even though it was 60+ years ago. That blowjob occurred in early adolescence, but the groundwork began in childhood where I first became friends with a neighborhood boy, Bobby, after we had moved to a new house and weeks later, he and his family moved in too.
In my neighborhood, in pre-school and for the first three grades of elementary school, all my after-school playmates had been girls and my mother had allowed me to wear panties and play dresses just like they did. I was around nine when we moved, and I decided I wanted to be one of the boys now that there were some around us. It was rough since I knew nothing about boy games and totally sucked at the ones I tried. However, one boy, Bobby, did his best to try to teach me and didn’t tease me as much as the others.
Then in sixth grade I had an opportunity to come to school dressed as a girl as a joke for a school carnival on the last day of the semester. At that time elementary school was grades 1-6 and the PTA wanted to have a party for the graduating 6th graders. The school said no, but . . . since the 5th and 6th grades were on one side of the school, and if we called it something besides a party, there was a way it could be done. They came up with contests between the two 6th grade and three 5th grade classes, a competition between larger, older kids, almost like a long recess, that the younger kids would never see.
Another boy and I both wanted to represent our class in the kite flying contest. My teacher, after checking with the other classes, said that if one of us wanted to dress as a girl as a joke, we could both win medals since there weren’t any girls entered in the kite flying. I jumped at the chance and the result – the change in the way the other students accepted me was startling. The same boys that had teased me for being a sissy now thought I was cool to have the guts to come to school dressed as a girl, and the girls were jealous.
Lipstick and rouge and stockings – OH my!
My teacher had envisioned me wearing an old dress of my mom’s over my male school clothes. Instead, I was dressed from the skin out in girl’s clothes and not just panties. I had on a padded bra, stockings and garter belt (a few years before pantyhose), slip, and a blouse and skirt. In addition, I was wearing makeup. The girls were not allowed to wear stockings or makeup to school but since my attire was considered a ‘costume’ it was okay. As soon as the grumbling stopped, they shifted 180 and I became one of the girls; invited to play with them at recess and again at lunch. Instead of Alan, they called me “Alice” and I for sure felt like I was in a wonderland. My teacher had put “Alice” on my nametag, and I’ll admit I wore it proudly. It reminded me so much of my happier days when I’d played with Carol and Ann and had felt so comfortable being a little girl.

This was a whole new era where girl’s clothes were concerned and the beginning of a new phase of my physical development at the same time. The times I’d worn girl’s clothes in the past had been almost environmental; sort of a when in Rome do as the Romans sort of thing. If you play in the snow, you wore snow clothes and at the beach you wore beach clothes and to play with girls you wore girl’s clothes. I hadn’t wanted to be a girl, just fit in with them, and had totally enjoyed it without ever having a thought of sexual arousal. Puberty was changing all that.
Being dressed as a young lady had my pubescent prick stiff as a stick all day. It hadn’t gotten hard when my mom had helped me dress, or when Bobby’s mom had put on the finishing touches but leaving their house and walking to school with Bobby had gotten me hard and I didn’t understand exactly why. There was a strange tingly feeling in my prick when I touched it lately, and dressing like a girl made my whole body feel the same way. Bobby teasing me about being his girlfriend seemed to add to it.
I remember wondering what he’d do if I asked him to hold hands. He’d begun when his mom decided I should wear a bit of makeup and commenting that maybe he should walk to school by himself, or everyone would think I was his girlfriend. I knew he had a crush on Heidi and wondered if he thought Heidi would be jealous of a girl that wasn’t really a girl? Didn’t make sense to me, but then at that point in my life, not much made sense and girls seemed to make the least sense of any of it. Puberty was changing them too.
Just a couple of years earlier they were good friends, much nicer than boys, and had welcomed me to play with them. If I happened to see their panties or they saw mine, it was no big thing. But when I’d insisted I had to wear jeans and boy underwear, I’d become an outsider to the girls and boys alike – some sort of sissy in-between the two – pretty much shunned by both.
Now a quick background on Bobby and the Collins family. Bobby’s older sister, Betty played a huge role in the things to follow. Betty was two years older than Bobby and Bobby was almost two years older than me because I’d skipped one grade and Bobby had lost one being a service brat. Bobby’s dad was Col. Robert Collins, USAF. His mom, Delphine, was a stepmom that adored the kids and they loved her. When I spent time at Bobby’s house she treated me like one of the family and I loved her too. They’d been too young to remember their mom when she’d died, and Delphine had met their dad while he was stationed in France as some sort of liaison with the French government. They had a picture of the Colonel and their stepmom flanking Charles de Gaulle who was related to her in some way.
The Colonel was in charge of some new project at Air Force Security Service and was gone a lot, much like my dad had been before we moved, but for different reasons. When Bobby’s dad was gone, I often slept over at Bobby’s house and if the Colonel had been gone for a few weeks and Delphine flew out to visit, Betty was left in charge. As luck would have it, that last Friday of school just happened to be a Friday where Delphine was headed out to the base to catch a flight about an hour after we’d left for school and was gone for at least a week. In addition, even before this idea of my teacher’s to have me and another boy dress as girls for a contest that none of the girls had entered, we’d made plans and gotten approval for me to stay at Bobby’s house the whole time Delphine was gone.
The reason I was excited about that was that on weekends, or any day she didn’t have to get ready for school, Betty would run around in little babydoll nightgowns when the Colonel wasn’t home and she was developing into a very well built young lady. Even when he wasn’t gone, the Colonel often went out to the base early on Saturday morning, so the first thing I did when I got up was look down the street to see if his car was in the driveway and if it was gone, I rushed down to Bobby’s house on the pretense of seeing if he was up yet. Betty wouldn’t think of dressing like that in front of a man, but us dumb little boys were deemed too immature to worry about.
As you can imagine in a military family, the kids had chores, and Bobby’s were mostly outside, like mine at home, and Betty’s were inside, helping her mom. Gathering dirty clothes to wash and vacuuming all the rugs were her two biggest chores. When she was done getting the wash started, she’d get out the vacuum and unless it was raining, she’d run us boys out of the house. After cleaning his room, Bobby had to cut the lawn every Saturday before we could do anything else. I had similar chores, so we’d often help each other.
For my carnival attire, my mom had supplied the blouse, skirt and a slip. The panties were mine from the previous Christmas when my sister had been given some she didn’t want, and I did.
There were seven in a package, all different colors, and each with a day of the week which appealed to my early onset, OCD type brain. I was not a neat-freak but developing a compulsion for organizing things and I thought having the day of the week on your underwear was fantastic. I was close to writing on my tighty-whities with a fountain pen when my mom stopped me. My sister didn’t like nylon underwear and had never opened the package of panties. They were a gift from an out-of-town aunt and a size too big but she couldn’t return them, so my mom had given them to me and bought my sister a package of cotton panties and we were all happy. I wore them frequently and always on the right day so that morning I was wearing the black Friday panties.
Years later when I first heard the term “Black Friday” for the Friday after Thanksgiving, my initial thought was that someone in the lingerie business had come up with the term but it was explained to me that it was from business accounting. However each year on Black Friday, I’m reminded of the Friday in May and the weekend at Bobby’s house.
When I got to Bobby’s house that morning Delphine loved the way I looked, and like others before her going back as long as I could remember, told me I should have been a girl, but insisted I needed some improvement. She dug out a bra that Betty had outgrown and some falsies she no longer needed to use that Betty said I could keep, and loaned me a pair of stockings and garter belt. In addition she insisted Betty let me borrow a pair of dress shoes that were a perfect fit to replace the sneakers I’d been wearing. She called me, “mon petit Aurelie,” for my blond hair, and some other things in French, but “Aurelie” became the first feminine name I was given. She wanted to do my nails in a color to match the lipstick she put on me, but didn’t have time, yet went as far as finding me a purse with a shoulder strap to put the lipstick in so I could touch it up after lunch when the carnival started and brushing my hair into a more feminine style.
It was the best day at school of any since I’d started, but with one problem. The boys, including my good friend Bobby, wouldn’t let a ‘girl’ in the ‘Boy’s’ bathroom. I tried to sneak down the hall when we all went to lunch but they were wise and waiting. After lunch I was sure I’d wet myself any minute and even gave it consideration. I looked for some place I could stand unnoticed and piss in my panties under the skirt but there wasn’t anyplace on the entire school ground.
My new girlfriends came to my rescue with a plan to use their bathroom.
The surest way to get sent home from school for a boy was to get caught sneaking into the Girl’s room. The plan they came up with was for us to walk around the corner of the building in a group and then use the outside door for the bathroom the younger kids used. It was a great plan with one flaw: No way was a teacher going to see a group of kids disappear around a corner and not go check to see what they were up to.
Now if I’d been thinking, I’d have gone in the outside door and out the inside door and down the hall to the Boy’s room, but I was letting the girls lead me and when we got inside there were just stalls with no doors. I was thinking it wouldn’t be a problem as I’d seen my sister use the toilet in a skirt. She just flipped up the back, pulled her panties down, and I never saw anything but a glimpse of her ass cheek. That was what I was about to do when my former 5th grade teacher came in and asked what was going on.
The girls had told me they’d watch for me, but no one stayed outside to do that. They’d all come inside to watch me instead.
Five girls and one boy dressed as a girl all tried to answer the teacher at the same time and it was too much. Ms. Preston was about to tell them to be quiet when they went silent on their own, looking at me. She turned to me and saw me standing in the door of the stall with piss running out from under my skirt and across the floor to the floor drain near where she was standing.
She sent the girls out as I began crying like the big sissy I was, and in between sobs, I told her what had happened and why. Elementary teachers always have hankies handy, so she dried my eyes and sent me to the school nurse.
The nurse was on the phone, the only one left in the office, since the rest of the principal and secretary were both out at the carnival. She asked what happened. I told her I’d had an accident and she wanted to know if I was bleeding. I said I wasn’t, but before I could explain what kind accident, she told me to go lie down in her office and she’d be in shortly.
When she came in she told me how cute I looked and I tried to explain that I wasn’t sick and how the boys wouldn’t let me in the boy’s room because I was dressed as a girl and I’d wet my panties.
In today’s world, doing anything that might humiliate a child would cause problems, but this was in the ‘50s. She commented that I was only the second one from my grade to have that problem this year and then followed the standard procedure which was primarily for the youngest students. She took off my wet panties as well as the garter belt and wet stockings and put me in a diaper and rubber pants. She wrapped my wet things in wax paper and put them in a lunch sack and sent me back outside.
So in one day, not only was I back to dressing as a girl, but I was wearing diapers again tool!
After school and we’d said goodbye to kids we probably wouldn’t see until after Labor Day, depending on which Jr. High they’d be going to, we headed home, planning first to go to Bobby’s and then to my house where I was to change and grab some more clothes for the weekend. Instead, we made it to Bobby’s house just as the first drops of what turned into a heavy shower fell on the area.
Betty was waiting and immediately I gave her back the shoes. When I handed her the bag with panties, garterbelt and stockings, she told me to hang on to them and she’d show me how to wash them in the morning. Bobby knew I’d been wearing panties since Christmas but Betty didn’t until I responded that I knew how to wash lingerie, my mom had shown me and I’d been washing out my panties by hand.
She looked at me with a funny smile on her face, then told me, “You must like being a little girl. You can’t go out in this rain to get some clothes, so I’ll get you something.”
When she went to the garage, I assumed she needed to get something out of the dryer. When she returned, she’d brought a handful of things and handed me some shorts and a T-top, saying, “You can keep the bra and panties on and wear these.”
Incredibly embarrassed, I had to admit the panties were in the bag, that I’d wet them at school, and that I had on a diaper and rubber pants, and that unless she had some panties for me to wear, the diaper might not fit in the shorts in her hand.
The top was pink, and the shorts were white with some frilly stuff on the hem. Betty informed me that they were some clothes, like the bra and falsies Delphine had given me earlier that morning, from a box in the garage that she had either outgrown or were for a ‘younger girl.’ In her mind she considered herself a young woman now and her body agreed with her mind.
“Keep the diaper on for now. I always wanted a baby sister. If these shorts don’t fit, I’ll find you some that will.”
Those cute white shorts were a snug fit and they made it clear I was wearing diaper, but we agreed they’d work for now and that I could go get some other clothes if the rain stopped.

Of course, Bobby was watching all this, laughing and cutting up until Betty turned to him. “If you can’t behave around your new girlfriend, I’ll tell Susan that you don’t need a ride in the morning. She said Kevin could take you if it’s raining. But if you’d rather ride the bus . . .”
Bobby got quiet in a hurry. The newest thing on his schedule that year was an appointment for an allergy shot late Saturday mornings. Working together, we could mow his yard and my yard, catch the bus downtown, and be back in time to have the whole afternoon to play in the woods behind my house – if we didn’t spend the day adventuring around the downtown area and eating one of the giant hot dogs from “Coney Island Hot Dogs”.
Susan was a year ahead of Bobby and me and a year behind Betty. That was close enough that they’d become best friends and Susan was often spending the night with Betty when I was spending the night with Bobby. Susan was much prettier than Betty but not nearly as well built - but she was getting there. I watched the Disney Mouseketteers show because Susan looked so much like Annette.
Susan’s older brother was Kevin and a sort of mentor to us younger guys. He was cool in a James Dean sort of way, had his own car that he worked on himself, and dated girls, making him, in our eyes, an expert in all the important areas. Plus he could be a pretty nice guy most of the time and didn’t mind giving us kids a ride someplace. Since it was three blocks to the bus stop on this end and even further from the bus to the doctor’s office downtown, a ride on a rainy day was enough to straighten Bobby almost instantly.
What got my attention was Betty picking up on Bobby’s comments about me being his girlfriend. I didn’t say anything but my mind went to my earlier feelings on the walk to school, and I went to change clothes as she’d told me, returning in a few minutes.
“You gonna wear lipstick all day too?” Bobby asked.
“It’ll wear off,” I told him sheepishly, getting a laugh from him and a smug smile from Betty. Like most girls, she seemed to recognize my femme side.
So I spent the rest of the afternoon and early evening dressed as a girl in girl’s casual wear – the teenage equivalent of ‘play clothes’ - and while Bobby just gave me a funny look sometimes, Betty’s attitude changed to treating me like a little sister, and it got better. I started wetting the diapers and knew immediately why I’d loved that feeling so much when I was younger.
When it got close to bedtime I had another clothing problem. When I slept over, I either wore my jockey briefs or pajamas and I had neither. Again Betty came to the rescue although I’ve never thought her intentions were entirely altruistic. She offered me one of her babydoll nighties and the matching bloomer style panties.
Bobby’s reaction was to make remarks like, “I can’t believe I get to sleep with my new girlfriend.”
First we had to take a shower and when Bobby was naked and I was down to my diaper and rubber pants, Bobby told me he wanted to pee in my diaper. I thought he meant put it on and wet it and I told him I’d been wetting it all afternoon and it was full. He didn’t care, what he had in mind was to pull out the waist in front and piss on my stomach, letting it run into my diaper.
At that time I had turned 12 and Bobby was 14, weeks away from 15. When we showered together it wasn’t unusual for us to fool around in the shower and one way we both enjoyed was peeing on each other. Let me explain how that started.

The previous summer, while playing in the woods behind my house, as usual we just stopped and peed when we needed instead of going home to use the toilet. We’d been in the early stages of puberty, comparing size and such, and stopping to pee usually turned into a pissing contest based either on quantity or distance. So I usually held it as long as possible to try to win either contest.
I’ve never been sure who started it. I think he did but he might have been right; maybe it was me. What happened was that one of us accidently peed on the pants leg of the other and retaliation soon ensued. Suddenly we’re jumping around with our dicks in our hands trying to piss on the other guy without being pissed on ourself. It reminded me a lot of the times in my youth when I’d wet myself on purpose so to be honest, I didn’t try that hard to make him miss.
In the Texas summer sun, we dried quickly and since we played until dark, when we went home we’d go straight to the bathroom to shower for bed. But then winter came and at a sleepover at my house Bobby held his bladder until we went inside and then in the tub caught me by surprise, hosing me down with a golden shower. I bitched, but the sudden erection I got made a liar of me and going forward it was pretty common for one or both of us to shower the other with piss prior to the one with soap and water. It was one of those showering sessions that upgraded our sexual knowledge, but not with a great deal of accuracy.
Bobby and I had both gotten ‘the talk’ from our dads when we started sixth grade and I often wonder if maybe the school had sent some communication to parents to remind them their little boys and girls weren’t such little boys and girls any more. However it didn’t stop his dad or mine from resorting to baby talk. Instead of calling a cock a cock, my dad used the ‘pee-pee’ term I’d heard all my young life and he called the female part her ‘slit’ instead of pussy or vagina. He tossed in some stuff about eggs and sperm that totally confused me and the gist of what I got was that if the stuff that comes out of my pee-pee gets inside a girl’s slit she’ll have a baby – DON’T DO IT!”.
The Colonel’s talk to Bobby was pretty much the same thing but we’d been at an age where we knew there was more but it wasn’t something of interest and we’d figure it out for ourselves when the time came. We’d already learned as much as our dads told us from kids at school and conversations with Kevin.
So back to the eventful evening in the shower with Bobby, a few weeks later, when we were peeing on each other, and a bit louder than we should have, we were saying “I’m gonna make you pregnant.”
Betty happened to be going down the hall at the time and couldn’t help but wonder what the two dumb-ass boys were up to now. She stuck her head in the door long enough to watch us pissing on each other and called a halt, embarrassing us both. She told us something to the effect that we were dumber than dogshit, that boys couldn’t get pregnant, and that it was cum, not piss that made it happen. Then she was gone leaving us bewildered. I wanted to go to her for an explanation, but Bobby overruled me and said we sh
ould ask Kevin.
As I previously mentioned, Kevin could be a pretty cool guy when he wanted to be. If none of his friends were around, Kevin was happy to have us younger guys hanging with him. So first thing the next morning we tracked down Kevin, explained what had happened, and when he quit laughing, he told us all about cum, the other stuff, the white stuff, that came out of our dicks when we jacked off.
“Jack off” was another of the terms we’d heard but didn’t fully understand and “playing with your prick” didn’t make much sense either. We’d both played with our pricks and even played with each other when they got hard, but always stopped when the feeling got weird. When Kevin offered a demonstration, we followed him inside.
Bobby’s cock was bigger than mine as I’d expected, and I was sure, as he pulled it out that Kevin’s would be the stage bigger. I guess at the time I was 11 or 12 and Kevin was 17. To my eyes his cock looked like a small baseball bat and I was in awe of it; even more so when after stroking it he began to spurt the mysterious ‘cum’ we’d heard so much about. There was something else he did that left a lasting impression on me. He caught the spurts of cum with his free hand and when he was finished he dipped a finger in the white puddle and brought it to his mouth to taste it, telling us that some people really like the taste and offering us the opportunity. We both declined, but went away anxious to get home and begin stroking our dicks.
Less than a week later Bobby rushed over to tell me he’d done it and it was awesome. I told him I’d been trying but when I felt like I was close it felt really weird like I was going to pee all over the place and he assured me that wasn’t the case. He said to keep going that in fact he’d done it several times and it felt more awesome each time. So I asked if he’d tasted it like Kevin had done and he told me he didn’t think you were really supposed to do that so he hadn’t.

So let’s move ahead to the night I was given the nightie to wear. A lot of times wearing the panties I’d gotten from my sister the previous Christmas had been all it took to make me hard and the babydoll and bloomer panties had the same effect. It wasn’t nylon like the panties but worked as well with one problem. Wearing nylon panties, I could point my stiffie straight up and it made a small bulge. The bulky bloomer panties had room for my prick to point almost straight out and made a very noticeable bulge. Bobby laughed at me but Betty gave me a little hug and told me to ignore him, that there was nothing to be ashamed of. Then, like so many before her, she reminded me that, “You should have been a girl.”
Had I known at the time what a lesbian was, I gladly would have agreed with her, since I had a huge crush on her. I was filled with thoughts, fantasies, and emotions that all seemed to be in confliction with each other. When Bobby asked if I liked being a girl, I’d told him no, that I was just enjoying being silly and acting like one. However when I got the same question from Betty, I admitted I did like it. Adding things like, I’d like to be a girl if I could be as pretty as her, didn’t hurt, and when she asked if I’d like to be her little sister, I gladly accepted.
That began the following morning. I usually went with Bobby. At that age riding the bus downtown and running around the strange streets and tall buildings was an adventure. But when Betty suggested over breakfast that I should stay behind to help her clean house, I jumped at the chance and it set a precedent; one that dovetailed nicely with my sexual adventures with both of the Collin’s teens.
With Betty, it began in a way with doing the laundry as soon as Bobby had gone. Betty instructed me to gather all the lingerie, including the panties and bra, slip and garter belt and stockings I’d worn the previous day. I began with the clothes hamper in the bathroom and knowing the panties I pulled out of the hamper had to be hers, the ones she’d worn the day before, I smelled them.
The story among the guys that were supposed to know these things, like Kevin and his pals, was that pussy stunk. If a girl let a guy get his hands in her panties, it was called, “Getting some stinky finger.” Another one I’d heard in reference to eating pussy was that, “If you can get past the stink you got it licked.” Bobby didn’t particularly like Kevin but he fascinated me. When Kevin’s friends were around, Kevin teased us but I’d had that going on for years so it didn’t bother me like it did Bobby. There was a benefit to enduring the teasing when his friends were around - instead of asking dumb questions I could just listen to the older guys talk about girls and sex and learn a lot.
I’m not sure if I got myself caught on purpose or if it was really an accident, but I had my eyes closed and the crotch of Betty’s panties pressed to my nose when I heard her ask what was I doing. So I told her about the stories I’d heard and told her I didn’t think it was true, that her panties smelled real nice.
That began a progression over the next year or two of my sniffing her panties, then smelling them with her in them, then smelling her without the panties, to licking her pussy. She loved for me to lick her and I loved doing it but she made it very clear that if she ever suspected I’d told Bobby or anyone else, even wild animals wouldn’t want to chew on what was left of my mutilated body! So Bobby never knew what I’d started doing with Betty and for all I know, never did find out. However she did find out, thanks to a slipup I made, that I’d been having sex with Bobby but I never told her how much or how long.
By the time of the 6th grade carnival, Bobby and I, in our sexual adventure with each other had gotten to where we fondled each other, rubbed our pricks together under the guise of comparing size, and more recently had jacked each other off. Kevin and his friends had once called me, “pussy lips,” and I’d ignored it. I did think my lips were bigger than other boys so that was just one more name to add to the list of things I’d been called. When Bobby had seen me with lipstick, one of the first things he’d said on the way to school was that if Kevin saw me wearing lipstick he’d think I was a pussy lips for sure. What I didn’t know and Bobby did and didn’t explain for some time was that calling me pussy lips wasn’t about the size of my lips. They were teasing me about being a cocksucker. It was that fall, as new 7th graders, that I earned the name.
Once again Delphine was gone for the weekend and I was staying at Bobby’s house while she was gone. We had orders to have the house spotless as the Colonel was probably coming back too and she’d call Betty when she knew for sure.
We all worked to make the place as clean as possible and Betty damn near became a tyrant. Susan was spending the weekend and knew about my helping Betty and she was made to help too. Betty sounded more like the Colonel than the Colonel did. Then when she was satisfied we’d achieved near perfection, and Bobby was back from his allergy shot trip, she threw both of us out of the house!
We’d both gotten new bikes at Christmas so we took off for the area where the Medical Center is today and played around one of the stock tanks all afternoon. We didn’t go skinnydipping like we sometimes did but did manage to get pretty muddy in the soft gooey mud around the edge of the tank and when we got back, Betty made us undress in the garage and go straight to the bathtub and that’s where our old fondness for occasional pee play made it happen.
I was expecting something to happen from the look in Bobby’s eyes. We were standing in the tub facing each other, our cocks getting hard, when the drain stopper slipped off the edge of the tub, bounced a couple of times, and landed in the drain – a million to one shot. Since I was on that end of the tub, I dropped to my knees and reached behind me to retrieve the plug and that’s when Bobby stepped as close as he could and began to pee in my face. I had a bar of soap in one hand and the plug in the other and didn’t want it in my eyes, and without a second thought opened my mouth and closed it over the end of his dick. I probably swallowed some but let most of it run out of my mouth but we both knew a line had been crossed. I’d had his cock in my mouth and kept it there for maybe a minute, long enough for him to stop peeing and get a full erection. Then I stopped, got to my feet, and tried to laugh it off while he teased me about ‘Aurelie’ liking his dick and drinking his pee and how I should do it some more so I could taste his cum. For a brief second I considered it and then we both laughed it off.

At the time, Bobby had bunk beds and he could never decide which he liked better. He’d sleep in the top bunk for a few days or few months and then suddenly move to the bottom. After a bit, he’d be back on top. When we’d started jacking off, we’d be in the bunks and neither could see the other but then when we decided it would be more fun if we could watch what the other was doing we’d sit together of lie together in the bottom bunk and being that close it was almost inevitable that we’d want to try jacking each other. Holding his cock for the first time had been so exciting I nearly shot off and he barely had to pump mine to make it happen.
So after pissing in my mouth in the tub, and my keeping his cock in my mouth after he stopped pissing, I was sure it would be what we’d talk about when the lights went out. Previously, we’d sort of danced around the idea of what it might be like to try sucking each other – not cumming because we knew that was bad – but just seeing what it felt like. Now I’d done it and Bobby wanted to know all about how it had felt and if I’d like to do it again and maybe more and then Bobby again brought up my dressing as Aurelie and being his girlfriend and one of us, quite possibly me, suggested that if we pretended to be a girl for the other guy then it wouldn’t be like we were two queer boys.
That is the sort of logic that makes total sense to boys, anxious to experiment in puberty and to some grown men if they’re horny and had a few drinks. Within minutes I’d gathered up my nightgown, panties, and the lipstick that was still in the old purse in the back of Bobby’s closet and I’m sure it was more the heat of the moment than any natural ability at sucking his cock that made Bobby cum almost instantly. Then it was my turn and he put on the nightgown and panties and sucked me.
Another of the stories we’d heard from Kevin and his friends was something like, bad girls would suck a dick but good girls swallowed. In my mind, if I was going to be a girl, I wanted to be a good one so hadn’t hesitated to swallow Bobby’s cum. I remember my thought was that it didn’t taste good. It didn’t taste bad either. It just tasted like nothing I’d ever tasted before. Since I’d swallowed the cum without a second thought, Bobby had done the same.
The second time, that same night, we convinced ourselves that Bobby didn’t really need to wear the nightie. We’d heard that there was a thing in a girl’s pussy that was almost like a small dick and since I had a small dick in my panties I could just stay dressed as the girl and Bobby would pretend he was eating my pussy. That saved a lot of time and trouble passing the nightie back and forth and it also left me to be the girl when we woke up the next day and like a good girl, not only did I suck my boyfriend’s dick for him, I swallowed!
We continued that charade for a few weeks but our pretense for it all was getting weak. I was a lot more enthusiastic to suck Bobby and he was beginning to think we were getting a little too queer. We needed advice and of course there was only one person to ask.
Without seeming to be too curious, or give away our reason for asking, we asked Kevin exactly what it was that queers did when they had sex and his explaination, flawed as usual, was enough to put us at ease. According to Kevin, queers butt fucked and swallowed each other’s cum.
Using the same logic that had made it not being queer since I was being a pretend girl, we determined that as long as we didn’t butt fuck or swallow cum, then what we were doing, especially if I continued to be a pretend girl, was okay. So from that day forward we kept a trash can next to our beds and if we were in my bedroom or his, when we were rewarded with a mouthful of cum, we’d go spit it out.
What Bobby never knew was that I’d reached a conclusion of my own. I thought it was more important to be considered a ‘good girl’ in my mind and as long as no one knew, I’d swallow the cum and then pretend to spit it out.
When Delphine returned the following Saturday, I’d again spent the night wearing the babydoll nightie and was busy helping Betty clean house and do laundry and Delphine was so proud of her “Aurelie” and seemed to agree with Betty that I made a perfect little sister for her.
And that opened the door for what was to follow with Betty.

When I tell people that I began cross-dressing before I was born, I get a mixture of reactions but none of them are belief. Yet it’s true. Even before I was born I had a full layette of baby girl’s clothing and accessories, all in pretty pink.
How it happened is that my mom was fully convinced, by tea leaves or a witch doctor or just a hunch, that I would be born a girl. She insisted that all her baby shower items be for a little girl so from the moment of birth, I was wrapped in pink. That might account for it being my favorite color today.
For the first eight years of my life my dad traveled extensively so my mom had a free hand to continue to treat me like her baby girl while my dad was gone. In my toddler years I always slept in a nightie because it made changing my diaper easier and when it was time to potty train me, I was trained not to have messy diapers but wet ones were allowed and possibly encouraged. That would come back to haunt me at various times in my life.
I was four when my sister Gwen was born and my mom finally had the little girl she’d wanted. I was kicked out of the nest and sent out to play with the neighbor kids and they were all girls. There were no boys anywhere close to my age but I didn’t mind – I felt more like one of them anyway. After years of hearing how I should have been a girl and how pretty I was and how cute I looked in play dresses, I really didn’t want to play with the boys and in a way, it got even better after I started school.
I had to go to school dressed as a boy but was allowed to put on a dress after school and because of my ‘wetting’ problem, I wore panties in the daytime and diapers at night. My wetting problem is almost a story in itself and was never a real problem.
When my sister was born my mom told me I had to stop wearing diapers, that I’d be starting school soon and they wouldn’t take me if I was still in diapers. I’d grown to love my wet diapers and according to family friends and relatives, I used to hide from my mom so she wouldn’t change my wet diapers. I went along with it until one night a few months after I was considered fully potty trained, I accidently wet the bed and my mom made a huge mistake. She told me if it happened again I’d be put back in diapers. I was hoping that was a promise but acted otherwise.
A few nights later, as soon as I was in bed, I wet myself because I wanted to be wet when my mom woke me. I think it took two or three more times before she made good on her threat, but only partly. She concluded that I was way too big to be diapered, but since it seemed like I needed them, I was also old enough to diaper myself. She was right. A six-year-old boy is fully capable of folding a cloth diaper and pinning himself into it. And if he happens to like his diapers thick and wet he can use extra diapers and make them that way. I think she thought I was doing it on purpose to get her attention, since she spent all her time with my sister. When I agreed to diaper myself, she figured I must really need the diapers.
So for the next 2-3 years, I’d wet my diaper a few times a week as soon as I was in bed. If I didn’t wet it then and fell asleep before it was wet, it would be dry in the morning. What I really loved was weekends when I could get up on my own, still in a wet diaper and nightgown, wet it some more, and go play with the girls.
That bedwetting ruse worked so well I came up with another one. I’d gone from diapers to training pants to tighty-whities in just a few months, almost without an accident. Then one day after school, I’d forgotten to use the boys’ room before heading home and wet my pants. Carol and Ann, my two playmates, had gotten pretty panties as part of their new school clothes and I’d campaigned for some, especially the colorful nylon ones that Carol wore, but my mom wasn’t buying it. So I tried a new track.
I told her the jockey shorts felt just like a cloth diaper or training pants and if I could have nylon panties like Carol wore it would remind me not to wet myself. It’s hard for me to believe she was so gullible as to fall for that, but the bottom line was me getting pretty panties that became my underwear for the next couple of years.
At school, I was made to play with the boys and hated it. At home I could change into a play dress and play with the girls and loved it. Then we moved to Texas.
These boys were awesome! They were just as rough and tumble as the boys I’d previously encountered and probably more so. But they weren’t mean or nasty. It was a country school and one of my classmates rode a horse to school at least once a week. Suddenly I wanted to be one of the boys. No more panties. No more diapers or nightgowns or play dresses. I wanted boots and blue-jeans and t-shirts.
It was tough, and I got a lot of teasing because it was really hard to hide my sissy beginnings, but I was managing okay, mostly because of the help of a new boy in the neighborhood that was almost two years older but in the same grade. His dad was in the Air Force and an ill timed move plus a school in Germany being behind the local curriculum had put Bobby and I in the same grade and same class. He took me under his wing and taught me how to play baseball, football, and do ‘boy’ things like ride a bike. I was well on my way to being a regular young man, entering puberty, and looking at girls in a whole new way, when a couple of seemingly harmless events, a Christmas gift and a school carnival, changed my life.
The gift wasn’t for me though I wound up being the ultimate beneficiary. One of my aunts sent my sister a package of panties for Christmas and she didn’t want them. For one thing, they were nylon and my sister hated nylon anything. In discussions years later we concluded it was because of a nylon nightgown and a wool blanket earlier in her childhood and getting shocked every time she touched something until my mom gave her a cotton gown to wear. In addition, the panties were too big for her.
However, I loved them! It wasn’t because they were panties – I didn’t wear panties any more. And while I did admire all the beautiful colors with lace edges – so much prettier than my all white jockey shorts, there were seven in the package and each had a day of the week embroidered on them.
I’ve never been a neat freak but great at organizing things and having a different pair of underwear for every day of the week made incredible sense to me. I was well on my way to being OCD about some things so I decided I was going to take seven of my underwear and write the name of each day on one of them with a fountain pen. Had I been successful and my mom hadn’t noticed, you can imagine what might have happened to the white laundry and things like my mom’s white blouses and my dad’s white dress shirts. Fortunately she caught on to what I was about to do and I explained myself.
After thinking it over, my mom said she knew I didn’t wear panties any more, but that my sister would never wear them, that they would fit me, and at least they’d go to some good use and she’d buy my sister some cotton panties, something she planned to do anyway. So after three years of being all boy, I was wearing panties again and wondering why that made my little boy pecker get hard.
Then five months later, on the last day of school before summer break, I became a full- fledged girl for the day and that’s a story in itself so I’ll save that for the next chapter.